Ok, let me set the stage here first. I have been texting for a few weeks with a really cute POT SB. Due to the holidays and her getting sick for a while it takes us about three weeks before we finally meet which we did the night before last.  

And fucking original requested a Substantial amount and showed me her Student Loan debt that was about $40,000.  She was very happy to fuck me every week for $300 plus a bottle of wine some snacks and a Plan B pill. So, I would make her a similar proposal.

She countered with she "needed $3,300 by January 29th to stay in school"

...of course. It just won't ever happen.
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As in many SD/SB relationships, you (that is "we") have the advantage of life experience and knowledge that the SB does not possess. We know that virtually all colleges will have some kind of payment plan, loan program, and hardship exception process for financially challenged students. It's in the school's best interests to keep students enrolled and attending class.  So I might just ask her a couple of questions to nudge her in the right direction to find out what the school's alternate payment plans are and I'd stick with my original offer. I'd might also point out that a few Benji's on a weekly basis can add up to $1k+ in a month and suggest that she can look forward to paying off her tuition within 90 days if she "manages" her cash well. Of course, she will NOT manage her cash well and will probably piss much of it away on crap she doesn't need and tequila shots with her BFF's.  
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With that I'd expect her to put me on hold, while she tries to target some other SD's for the whole $3k. Once she realizes it ain't going to happen she will come back to me. Why back to me? Because I actually spent time "mentoring" and "coaching" her through a difficult issue rather than just insisting she whore out her pussy for cash. So if she can't get the full $3k upfront I become the better choice for an ongoing arrangement as I really do (as far as she can tell) care about her as a person, blah, blah, blah...  
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Or she finds a newbie SD dipshit or uber-rich a-hole who gives her the full $3k upfront. She will bang him once then mysteriously be unavailable to him - until she needs a car, or a rent payment, or a boob job.

Is this a question of how to close the sale?   I don't know.  You might be in a bidding war.  The guy that offers $50 more will win.

Is this girl going to Truck Driving school that she can attend classes with having some type of agreement in place for her tuition. OTOH you could fork over $4,000 to cover tuition and some incidentals just to be a nice guy. Since it’s not my money I recommend you take the risk but if it were my money I stick to my original proposal and if does not respond then it’s the next SB up to check out.  

I told her I would sleep on it, as if there were ANY chance of a lump sum payment. lol. And then I told her that I couldn't commit to anywhere near that much money without knowing if we were going to "click" I suggested we see each other once more for a "real" date. I would give her $200 so it wouldn't be a total loss for her if it didn't work out (see, I am not a TOTAL jerk. lol) and that AFTER we had gone BCD at least once we could talk about the future.

Even though my contract concept was met with near universal disapproval, one of my provisions would dovetail perfectly in this situation.  I would simply cut her a promissory note for the $3300 (a pittance for we gentlemen) with very generous pay-per-meet payback terms, say 15 bangs to retire the note.  Now sure, she could walk but you could always threaten to take it to the Dean or something equally farfetched with the idea it would way heavy on her mind. With SB logic being what it is, I wouldn't be surprised if she would actually honor the terms and it would be a win-win outcome with smiles on everyone's face.

Good move, Gambler!  Remind me not to play poker with you!

Sounds like a good strategy, considering your overall objectives.  Your observations about her online activity post $3k demand were an important part of the process. That meant she was indeed searching for an alternate SD and likely only found failure.  
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Not sure that would work for me, but I might try it on a POT SB in the near future.  
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I am going through a similar process with a POT now, though on a MUCH smaller scale. I travel to a city north of me about 2 to 3 times a quarter, so I decided to hook up an SB in that city for a hook up when I'm there.  Sent out about 6 messages to profiles I thought looked like semi-pros and hoped I'd catch a M&G with one or two. Bingo!  22 year old, petite and slim POT responded and we moved to text chat. I suggested a M&G for drinks at a popular place and she agreed on the day and time.  Thought I'm good to go and started thinking about how to convert to BCD either the night of the M&G or the next day. But then she texted me again: "Oh and what will my allowance be?"
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I replied that I only discuss allowance once we've met and agree that we both like each other. Not expecting anything other than talking and getting to know each other. If we both like each other we can make sure we find a mutually satisfying arrangement.  
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15 minutes later: "Ok that sounds fair, will you cover gas expenses for sure?" Now I'm irritated. But I reply I'll cover $30 for gas and parking if any, drinks are on me.  She asks about parking costs. I tell her there's free self parking and Valet for $10.  BTW, this tells me a few important things about her. The place I selected is in a very well-known and popular area. She says she lives within 10 miles of it but doesn't know the area, the parking situation or the restaurant/bar I suggested. I've had more than one POT SB meet me there that ended up not living locally, even though their profile says they do,  I find that irritating as well.  
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She replies: "ok well can we make it 50 just to be safe?"  Now I'm ready to just bail, but I counter with: "I appreciate your concern not to have your time wasted. I am not that guy. Let's call it $40 and look forward to a successful meeting, please."  
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One hour and 10 minutes later: "Ok sounds good".  If she had pushed back any more I'd have dropped her. And if I'm not totally smitten by her when we meet on Monday, I'll probably drop her anyway. I expect that if we do start negotiating she's going to try to high-end me and I'll need to navigate carefully through her GSP attitude.  
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Key observation for newbies: When I deliberately changed my communication mode to a more stern, authoritarian, and annoyed voice, she ultimately (and correctly) realized that I was getting pissed and she needed to back the fuck up.  
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Lesson 1: Don't lose your balls just because she's potentially a hot piece of ass. Man up and demand respect. That does not mean be a dick. It just means be firm and don't let yourself get pushed around.  
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Lesson 2: Once you communicate a decision/offer/definitive statement or requirement, STFU and do not say anything else until she replies. If you come back with a "softer" message 1st she will forever own your balls. Patience wins the tough negotiations.

It's  a mile wide and only an inch deep, now THAT is shallow. lol

This is a fuck board. What do you expect?

Situation with several SB’s that wanted a minimum of $500 to $600 per meet. I told them I would think about it and when I responded back a couple of days later with my original offer all I got from them was to wish me well on my search. These were reportedly veteran SB’s so you may have a different outcome.

Make you a deal, just say some dickhead friend of mine proposed that I have you sign a note for the $3300 and she what she says!

I'm a newbie to SA but not nearly to,women or life.
In my first few weeks on SA...thx to Mr F's guidance...I've decided that the really young ones are cute as hell, have no life experience, little sexual experience and are as flaky as they are in civvie life.
I like the ones that have been around a few months.
Their delusions of grandeur are gone, they've figured out the majority of SDs contacting them are flakesand they need money.

The problem isn't her signing some unenforceable, uncollectable promissory note. The issue is what can I do with the note besides wipe my ass with it when she ghosts on me?

I just say Im sorry but I can only do this much. I tell her be safe and take care. I usually get a much lower counter. If not I dont really give a fuck. Of course there is always the occasional lady that goes BSC at my offer and wish I would die. I get over it and move on.

and I mentally predicted what both of you would say,  not surprisingly neither of you disappointed. lol

You really ARE Tom Hopkins!  LOL :p  
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You are spot on. I and I have had extensive sales training. Though I've never been a sales rep, I have worked in many adjacent, supporting, or leadership roles within sales orgs.

Ive been in sales my whole life. The problem is easy to identify.  Some of these SBs have s rather high opinion of the value of their pussy. The solution is easy. Accept less or move on. Lol

Had almost the exact encounter last night with a POT SB.  She texted me today and tried to pin me down on price. When I finally said my experience has varied from x to y with the differences involving how many visits and level of transportation assistance, she came back with a range of 750 to 1,000 for per meet. I wished her good luck and moved on.

Thats why I always try to find out if we bcc are even ijn the same universe as to what they want. Why waste time and money if its not even close?

I think a period of radio silence would be in order.....first one to contact loses.

I love having dinner/lunch with new POT girls so there's no investment here. And yes, we all want to at least fuck once and most of us are willing to offer a bit more for the first time before you either cut her loose if the chemistry was missing or re-negotiate if she is a keeper. It depends on how cute she is, and how favorable the logistics/schedules are. So if she is a 8/9 on TER scale and lives close by then it's all positive. I would tell her straight up that all her tuition upfront is not possible no matter how much I want to help her but I would definitely help her figure it all out if we start our mutually beneficial relationship as I like her a lot and feel that our arrangement can be long term. I would suggest a weekly allowance to begin with for meeting 2-3 times a week and offer 500 for first week. That way she would like the number better than what most will offer for a single BCD meet.  
Again, it depends, if she is just a 7 on TER scale and lives far away then I may not even see her for a dinner

Met with POT SB for cocktail M&G. Conversation went well, she seemed nice. Wound up driving her back to her place, which I instantly recognized as a pricey new development. She’d mentioned her prior SD gave her rent money, plus play money, plus PPM. I asked why he and she weren’t together anymore. According to her, his ‘circumstances changed’ (he was married, btw, and owned his own business which supposedly was seeking a downturn in business), and he told her he couldn’t do it anymore.  

and simply posing a question for the board. I had already decided how to handle this well before making my post on the board.

LOLOL Just take their "advice" grandpa... You're kinda new at this anyway right?

But then again I am waaay underfunded compared to most here apparently, also less picky. A 7 suits me fine as long as the performance is good.  While I don't go for ugly or obese (hell if I wanted that I'd stay home and/or just JO ),  I will see "less perfect women, agewise (up to mid 40's), a bit of baby fat or MILF muffintop.  While I have had some Sugar dry spells, I generally get $ 100-200 BCD "dates" on a fairly regular basis (and thats in the NY/LI area).  Then, with my savings I save up for a 2 hr extended date with my ATF provider (a 9/10) and am simply satisfied all around.  I go for quantity AND quality, just different women.  The SB's are booty calls rather than GF's, though we spend on avg 2-4 hrs BCD.  At one day a week during daytime hours only its a narrow window, but it works for me, and for the gals I see apparently.

LOL at MILF Muffin Top & I go for quantity AND quality, "just different women" -  

On fhat same nkge I have had some hot POT TER 8-9's @ 19 y.o. as well sprinkled in.

So we agreed to meet on Monday night at 7. I landed at 5:30 and just had enough time to check in to my hotel and drive the rental to the bar/restaurant. As I got near the hotel she texts and asks if we can delay to 8 pm. I agree and now have an extra hour at the hotel.  
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I leave for the bar with enough time to be 15 minutes early (as usual) and arrive at 7:45. She's not there yet and I order a glass of wine and start to text her that I'm early. As I'm typing she texts me that she's running late and wants to try 10 pm. That's too late for me. I have early meetings in the AM so I tell her no and how about tomorrow?  She agrees on 7 pm same place and says "I'll make it up to you". (Never heard THAT before! I head back to the hotel, out of pocket $24 for a glass of wine and valet parking, and an hour round trip travel time. Stop at an In-n-Out on the way back and enjoy my Double-Double - alone.  
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Next night I text a confirmation at 5:30 and get a positive response.  Get to the bar at 6:45 and she texts at 6:58 that she's parking. Took her a few to find the place (located in an outdoor upscale mall) and we sat down at the bar at 7:05. All seemed well. She's sweet, slim, a bit shy and very, very cute. Me LIKEY! We chat about various topics and eventually I steer the convo to why she's on the site, etc. She says she's new - well she was on a while ago for a few days but stopped, then restarted a few weeks ago. Says I'm the first meet she's had from the site.  We keep chatting and I ask if she'd like dinner. Yes. We order at the bar and keep chatting. Now she opens up a bit. She's actually had 2 prior arrangements. The fist was not great, but the second ended recently on good terms. He was giving her a monthly allowance and  at first they would meet weekly... then the tempo slowed as he "got more busy" and the meets went down to once or less a month. He eventually ended it as he "just didn't have enough time" for her.  So now she is hoping to get a new SD with the same arrangement.  
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I'll pause here for two observations:  1st - She said she was essentially new on the site, but had 2 previous SD's. So she's 21 now, barely. That means she had SD's as early as 19.  2nd- She said the reason she was delayed the night before was that she had just moved to the "area" that day  - from a city 145 miles away. That means she was in the other city when she reactivated her profile.   And her new location was still 25 miles north of the city on her profile.  Two (I'll be polite and call them) conflicts that were not really explained.  
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Now dinner progresses and I dig for more info.  How much was the monthly allowance?  She held up her napkin to her mouth so the bartender presumably couldn't see her and said $5,000 a month.  
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Silence.  
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More silence.  
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Finally, I said "Do you still have his number?" She did. I said "Call him - now. Or, give it to me and I'll date him for $5 grand a month."  I was smiling while I said it, but I was thinking "WTF kind of idiot pays $5k a month, especially for an SB who literally lives in a low-rent market in the stix?"  She laughed, and I thought she got the hint that I will not be that SD. She did not.  
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As we finished the food, I let her know that I'm only going to be in the area every 4 to 6 weeks and would only offer her a per meet allowance.  She seemed ok, but of course we had not discussed the actual number. I told her we would not be going BCD that night, so we needed to work out what happens on my next visit. I paid the check and we went outside to be away from other people.  We got into details of what a "meet" would look like; time together, activities out and in doors etc. We seemed to be in agreement on the details and she asked me how much. I went with the "here's what my last arrangement was like" line and offered $300-$400 per. She countered with "can you do 5?" I thought about it; she was hella cute and submissive, seemed down for anything and everything I wanted sexually and I'd only see her infrequently. So I agreed on $5.  She seemed happy and I asked her if she had a recent test.  That's where it all fell apart over the next 10 minutes.  
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As soon as I asked about testing and birth control she said she'd need more to accommodate the "extra effort". Her argument was that it's more time and effort for her, plus more expense. I countered that if she had to pay for either of these through her current health plan I'd find her a local family planning clinic and cover the direct costs, but I'm sticking with the five hundred per meet. Her jaw dropped and she said "five hundred? I thought you meant five thousand a month?" I quickly made it clear that $5k was NOT going to happen. It's $500 per meet. She countered at $700 (for the "extra effort") and said she could not go lower.  And that's where it ended. I told her we should each take a day or two to think it over and the we can reconnect and talk some more. Gave her a nice card with the promised $40 and a hug. Then said goodnight and headed back to my rental car.  
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Final position: This deal is dead. I won't re-contact her. If she contacts me and agrees to my offer, I'm back in.  
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Clearly, I did not handle this perfectly. I ignored the early and ongoing red flags and tried to salvage a good deal from a poor starting position. It certainly did not help that some fucktard happily agreed to pony up $5k a month for less than weekly meets (assuming that was not an outright lie). But I could have stopped at the 1st drink and bailed without the $135 dinner check.  Another Double-Double would have been just $4.95 Little Head tried to win the day, and both Little Head and Big Head lost.  

No one paid her 5k per month!! Just wait and see what she comes back to you with...

but I do agree with you here, I doubt seriously that she ever got $5k a month either.

Agreed. In fact, I sent out 6 "I'll be in your area" messages about 2 weeks in advance. I was selective about who got messaged and didn't expect a high response rate. Still, this is the only bite I got.  
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My radar was working well enough to keep me from agreeing to her $700 ppm ask. That's just not going to happen with an unknown, inexperienced SB.  I didn't mention that she showed up to her M&G with a 56-year old corporate professional at an upscale mall with upscale foodie joints wearing sweats and sneakers. I'll give her credit that her leggings and hoodie were color matched and fit rather snugly. And her ass was amazing to look at. But she clearly doesn't get the "interview" component of M&G's yet.  
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I do think it's useful to share stories of success as well as failures. We tend to learn more from the failures, so share the pain and we all benefit, even the SB's.

I'd promise whatever you need to promise, hit it once for $700 and evaluate the worth of future experiences with her based on what your $700 date is like - going to in and out by yourself will eventually get old

you are a pig just as you claim! LMAO!!! Why can't I bring myself to do such a thing? I must be a pussy!

Recap: So we parted on Tues, Jan 16 with no deal made. We had all the per meet activity details completely  worked out and agreed to, but were $200 apart on the sugar. We each agreed to "sleep on it" and I left never expecting to contact her or to be contacted again.  
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Forward to the following Monday, Jan 22:  
By text (paraphrasing for brevity). Note: I decided not to mention the arrangement or sugar first:  
Her: Hey there
Me: Hi, how are you, etc.
Her: I'm good, drivng to work... etc. When am I going to see you?  
Me: Might be in town in 3 weeks. Don't want you to text and drive! I'l be open to talk more tomorrow morning.  
Her: Ok.  
I did not text her on Tuesday or Wednesday.
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Thursday
Her: Hey
Me: How's work and school, blah, blah, blah. ?
Her: It ok, just having trouble paying tuition
Me: Must be frustrating. (It's truly a thing of beauty to appear to be empathetic while probably frustating the hell out of her that I won't start the money topic.)  
Her: Yes, I need help!  
Me: So have you been thinking about my offer?  
Her: I want to go with it
Me: Thanks for reconsidering (Hey I can be gracious in vicotry, right?)
Her: When will you be back?  I need to pay by tomorrow.  
Me: Still locking down schedule. Looks like earliest is 3 weeks (I'm not scheduling my travel for her allowance.)
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And here comes what most of you see warming up:
Her: Do you think you can send me my 1st allowance please? I don't want to get dropped, blah, blah, blah
Me (after waiting a full 10 minutes): I understand, but I can't send in advance. Been burned too many times.  
Her: I get it. Just don't know what to do.  
Me: (I make some obvious suggestions: defer tuition req, pay day advacne from work, title loan on her car, etc.)
Her: Those wont work becuase, blah, blah, blah.  
Me: Hang in there, I know it's tough.  
Her: If you don't want to help me just say that.
A minute later:  
Her: It's alright I'll figure it out.  
Me: Ok. Just some ideas. I've been there and I know it's scary.  
Her: Right.
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So even though I refuced to pay in advance I wasn't a dick about and I came off as empathetic and trying to help her find creative solutions.  She will either drop out of school or actaully earn/borrow the money somehow. Who knows she may start stripping. :p Or she could find another SD.  But I think the next time I travel to her area I have a standing BCD (probably) available at my terms.