So, being new to this I wanted to ask about "risk." Specifically, how do you assess whether an SB just wants sugar but either doesn't know "what's up" or has no intention of keeping her part of the arrangement?

This is something that concerns me because in the hobby world, years ago in my past, I've been taken. Other than the obvious, what are the red flags you use to steer you away from women who's game is to take without giving?

If you assume they all will rip you off, you will be on your guard.  What's the old saying, trust but verify?
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Firstly you can't force them to do anything (that's known as rape.)  So you have to entice them.  I'm assuming here you are a stand up dude and will be honorable in your treatment of them.  
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So you make your verbal agreement and then pay them after they have performed to spec.
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If you are sending them money in advance, expect to get ripped off.  

To meet for lunch then you will most likely not seem again or they will jus want to meet for lunch and collect their easy money. The mention of  Cash app and PayPal included in their profile is also another sign. Lay your groundwork and stick to it otherwise you may fall victim to their scams.

I will NEVER send a penny in advance to a POT SB that I have never met, and neither should you.  

 
I also don't pay POT SB's simply for "showing up" and I almost never give a POT SB a penny until AFTER we had gone BCD. Sometimes if I know a POT SB is nervous about getting ripped off herself I will leave the agreed up "allowance" on the nightstand or some other place in plain sight so she can rest a little easier about getting paid.

 
As for red flags, those too are easy to spot, any mention of "send money" is a red flag, any mention of "pay before BCD" is a red flag,  any mention of being an unreasonably long distance from me is a red flag.  

 
Over the last four years or so I have broken a couple of these rules a total of four times. In one case I agree to give a POT SB "babysitter" money for our first date that did not go BCD that night, we would have gone BCD, but we ran out of time due to a long dinner we had at the restaurant, I ended up seeing her at least twenty more times, So I will count that one as a success. Another time I had to cancel a date on a POT SB, my fault not hers, She somewhat kiddingly asked me to buy her a pizza the next time, she gave me her real name and real address which was local to me, (maybe ten minutes away) so I said "what the fuck, why not?" and ordered her a pizza, we did meet in person and I saw her a few more times so I will count that one as a success as well.

 
The other two times were a POT SB who I had a date scheduled with the next night claimed that if she didn't fill up her tank "tonight" she'd be unlikely to make our date the next night. She was close to me and I did meet her, put about twenty bucks of gas in her car, saw she was a fatty and later than night I canceled our date for the next night, not a success by any means, but it was better than wasting a lot more time having a public date with a fat broad. lol Lastly was a POT SB who was a single mom, but didn't want to "put out" but was kind of cute and who had a life so fucking pathetic I gave her a few bucks after our "coffee date" just out of pity. I never got anything more out of it than the good feeling you get sometimes by giving a bum twenty bucks for a hot meal. lol

 
In ZERO cases have I EVER "sent" money in advance, to date I have had hundreds of requests using all sorts of excuses, some of them rather clever I will admit, but NEVER have I violated my only ironclad rule about "sending" money to a POT SB I have never met. If you adopt the same rule your chances of getting ripped off go down to almost zero.

I'm not interested in doing anything with anyone who isn't a willing participant. If I have to entice anyone, they are not an option in my book. I just simply walk away. I do not want "something for nothing."

I'm really more interested in people's vetting process.

Thank you.  This was helpful.

As GaGa's answer implied: Avoiding (or minimizing) risks equates to implementing and following rules. And just to keep things complicated, each rule can have exceptions:  
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1. Never send/give money in advance, and for fuck's sake never OFFER to send money in advance.  This generally applies even to ongoing SB arrangements. She asks for cash on Tuesday and your next date isn't until Friday. There's a huge chance you will be poor and horny Saturday morning.  
Exception: Small amounts during/after a M&G may be ok. Things like parking, gas money, of course the cost of meal/drinks are all ok IF you think she will be worth it. Risking $20-40 isn't really a big deal.  Other exception: I have, after a satisfactory M&G agreed to cover the cost of a full panel STD test. I take her to MY lab and pay the attendant myself.  
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2. Never agree to let her bring a friend or relative to the 1st M&G or scheduled BCD.  That friend could be a BF, pimp, carrying a gun or video camera, or just be planning nefarious actions you do not want.  She will say it's for safety, or her friend is her ride or some other reason. That's BS.  
Exception: Maybe, after you've had several successful BCD's she suggests bringing a hot friend. Again, this has increased risks, but also offers increased reward.  How to deal with sugar (if any) for the friend is a topic for another post. Note that although several of my SB's over the last 10+ years have suggested they are amenable to the idea, none have ever delivered.  
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3. Switching to Monthly allowance. You may reach a point where lugging around cash to each BCD or making multiple electronic payments gets tiring, or inconvenient. It's temping to set up a recurring monthly payment and then your "dates" seem less hooker-ish to each of you as you don't have to pay her after sex and it's more "classy."  Your risks are many:  
A. Being unskilled at handling money, she may (will!) call you at the end of the month with a cash emergency (rent, phone, car, etc.)  
B. Your allowance is based on X sessions per Y time period. She may (seemingly by no fault of hers) end up reducing the number sessions per time period - but not agree to an adjusted allowance next period.  
C. She will take this as her cue to grab and run. Getting all that cash upfront could motivate her to execute that rip off plan she's been patiently waiting for.  
Exception: You consider the risk worth it as a sign of good faith, and you want to "lock" her down for the long term. This is a SHITTY exception. But if you understand that your risk is a full month's allowance, then by all means...  
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4. Looking at your original question, I see the need to address the risks of your 1st planned BCD. What if she shows, but wont put out? What if she demands the cash upfront and could then make some excuse and leave?  Both of these have happened to me. Rule: Always have a specific, explicit discussion before, during or right after the M&G that talks about what each future meeting's itinerary includes. If you don't hear her affirmatively consent to fuck, go full stop until you do.  
Exception: Nope. Not this one. She agrees to fuck or there's no BCD or allowance.  
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Having said all that, there will always be risks. You need to continue to develop your "Spidey Senses" as you go. If she asks you to do something that makes you uncomfortable, ask her why, ask her why again, and again until you get to the (probably) real reason.  
Example:  
You: Why do you need more money this time?
Her: I need to cover my rent.
You: Why can't you cover your rent?  
Her: I ran out of cash.
You: Why did you run out of cash?
Her: My other SD didn't pay me, OR
Her: My roommate can't pay her share and the lease is in my name, OR
Her: I went to Vegas last week and lost $400 on blackjack, OR
Her: I really want to buy these cute shoes! OR
.. you get the idea.  Then you have to decide if you trust her or not. Hint: You WILL be taken at least once, so don't pay until you can lose the cash.  
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Hope this helps... because:  
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Life is good
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The Cat

The O.P. asked questions we've all struggled with and you would be well advised to listen to the excellent hard won advice given by Gambler, Herb, et all.  I'll just add a few points.

1. I've learned the hard way not to leave her $$ out in plain sight.  One time a SB I'd already had a fabulous BCD session with came for our second date and when she saw the $$ I'd left out she took it while my back was turned, made some lame excuse about having forgotten something she needed in her car, and drove off!  Classic cash and dash. I still don't get it since she seemed to have as much fun the first time as I had and appeared really enthusiastivc about a repeat performance.  Oh well...

2. Never send $$.  Like, never.  OK I'm just repeating what others have said, but I've broken this rule myself a few times and NEVER had a good outcome.  So. Just. Don't.  Right now many people think the health risk of meeting irl is too great I concur.  But many SBs seem to think that makes asking for $$ for pics and videos ok.  It does not.  Why the fuck would I pay someone for naked girly pics?  Haven't they ever heard of internet porn?  There's so much free stuff available online you couldn't watch it all if you tried.  I get it that the SBs need $$.  I mean that's why they are migrating to SA in the first place/  If they are hot enough to get my attention they are hot enough to get laid anytime they want. So they are not here primarily to get laid.  They need $$ and the sex is just a bonus feature.  Don't provide $$ without the sex!

3. Never do monthly arrangements, only ppm and only after you've had some BCD fun. I know others here will make exceptions, but this one is a hard and fast rule for me.  there's quite a bit of psychology to this game.  I think a monthly allowance creates a bad environment for both SB and SD.  The SB feels obligated.  She's take your $$ but maybe is not in the mood today.  Wants more $$ so feels she has to show up and is bound to resent being put in that position.  You on the other hand start feeling entitled.  You paid her dammit so she damn well better show up.  I think those feelings of obligation and entitlement are a real buzz kill that never ends well. Otoh, when you do PPM, at the very least you know that when you both show up for a date it's because you both really want to be there. You both have your reasons, but you both want to be there.  Much cleaner and feels better.

4. Exceptions.  As Herb points out, rules do have exceptions.  Just be damn sure when you break one of your rules you are prepared for it to be a mistake, since that's usually what it is.  That said, I've had exceptions turn out very well.  One time I dated a truly stunning young woman for months, who then dropped me when her BF found out and bitched to her about it.  OK, time to move on.  A year later (!) she texted me saying she needed $500 to resolve a legal problem and had no one else she could turn to and I was always so nice and respectful, blah blah, and she would love to make it up to me.  I gave her the $ and somewhat to my surprise she fucked my brains out for several months, paying off her debt and resuming our original ppm arrangement until she disappeared once again.  I call that one a win and would not be surprised if she calls me again next time she's in a crunch!

This is all excellent advice and mirrors my experiences.  I also hide my wallet during the first visit BCD, because I’m always afraid of getting robbed.  The may be paranoid, but I think it’s prudent. Regardless of whether it’s a first or a repeat meeting,  I have the PPM money counted out ahead of time and put it in a pocket of my pants. At the conclusion of our meeting, I hand it to her.  I also put less than $10 in another pocket and hide any other money that I have. When I get the request that comes, sooner or later, for an advance on the next meeting for unexpected expenses (rent, phone bill, car repair, etc.), I show her the couple of bucks that I have.  They are not happy, but I have found they accept it better than just saying  no.  

This is also a good tactic to reduce risk. Although if she is really intent on robbing you, putting a gun to your head should make it pretty easy for you give up the cash.  :p  
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I, too, do this for 1st time BCDs. Since I almost always host, I take a few more precautions as well. I also hide may house and car keys. No sense in tipping her off that I have a car (it's parked inside my closed garage or on the street). I also keep my home stash of emergency cash and cards hidden away in an illogical (at least to her) place while I have a honey-pot cash box on my open closet shelf with less than $100 in a cheap wallet and some old cheap watches in it. I actually tape the key to the box - just to look too stupid to be careful.
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As for the allowance, I always count it out in advance and put it in a small unmarked envelope. The envelope is near my front door, but not obviously visible.  When I walk her to the door to say good bye, the envelope just seems to appear in my hand when I lean in for a good bye kiss and boob squeeze.  
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Life is good.
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The Cat

As a newbie to the SD/SB game, a couple of ground rules I've decided upon for myself:

1. I've decided to do cash only in an unmarked envelope. I like the convenience of the APPs but I'm not sure repeated payments in round numbers are such a good thing.

2. PPM only. Allowances just seem to scream getting ripped off maybe in the future if I met someone I really trusted, it could work but for now, nah.

3. It's good advice to hide cards, money, keys, etc. Thanks for that.

4. I'm ok with meeting for dinner and then hosting at my place for nookie. I like that in my place I know what's behind every corner. I don't like the feeling of being in an unknown environment. Maybe that's a little over the top but when the economy tanks, crime goes up and desperate people do desperate things. I don't need some boyfriend or pimp or druggie waiting to jump me.

I, too, am always super careful about hiding wallet and ID, etc. on a first encounter at my place for sure. And I place donation in a white envelope, usually have it on my coffee table. AND if I go to an incall, M&G or other scene to play, I have the donation in an envelope, some extra cash and one credit card only in my pocket for cabs and unexpected contingencies, etc. NO WALLET.