Quite often prospective SBs (or even existing ones) ask me for small sums of money..  My policy has always been a hard NO. I will pay for food, booze, and companionship  (sex), but I am not just throwing away money at you..  

 
I was thinking of perhaps rethinking this policy, and maybe allocating some budget for throwaway money. You might even call it investment in building that relationship or sustaining it.  We are not talking about exorbitant sums of money but maybe like $500 a year.  If someone texts me saying, hey.. Can you lend me $50 for grocery, instead if shutting her down like I do, maybe send her that $50..Is it better to have a middle of the road approach where you still say a hard NO to someone you haven't met yet, but send some money their way to someone you have spent time with?  

 
What do the better minds here think of this aspect of sugaring?  

My policy is the standard.  I'll pay for all date (food, transportation, tickets, etc.) and BCD expenses (i.e. hotel).  And will also, at my own discretion, buy "small" gifts (under $100 - clothes, lingerie, trinkets, etc.).

 
On the occasion that I'm asked for a small sum of money (again, under $100), for an ongoing and well performing SB, I give the money happily and consider it part of my gift budget.

I’ve been down this road twice before, analyzing it the same way you have. The first time, these small transfers acted exactly as I wanted them to…as investments.  They helped to build a straightforward ppm arrangement into a more open/trusting relationship…in other words not purely transactional with payments only for BCD activities. Not once during this new territory did I feel that she abused my generosity or took it for granted.

A second time with a new SB I approached the request in the context of my prior positive experience. I moved forward with the small occasional transfer… and it worked for awhile. But, things changed and so did the flow of our arrangement.  I just did not feel like the transfers were building trust. They just felt transactional. So, just as we know there is no such thing as “going back” in a sugar arrangements, that one had to end. The only remaining, and unanswerable question is: “did my decision to provide small additional help hasten the demise of the arrangement, or would it had ended if I said no to her requests?” Or, was it destined to end soon anyway? Who knows…

One of my SBs became a provider. I introduced her to TER and wrote her first review. She has great reviews on TER. I still pay her the ppm we agreed upon six years ago. She charges her clients that amount hourly, while I can stay until I have had enough sex. She is a single mom with a one-year-old boy, so she often needs financial help. I help her here and there as a thank you for the many extra hours she gives me.

I think we all agree here that you don't send money to someone you haven't met. Ever. You're almost certain not to see them.
For the existing SBs,, we've all been there and the rules may not be as firm, with some leeway if it's a valued SB.
But....
My sense is that if you're getting a lot of these requests you are dealing with "needy" SBs that might not be the best ones for the long run. I personally prefer SBs who have a stable situation, usually a real job (some exceptions for students) who are not going to nickel and dime you. These are generally gals who want to have some fun and upgrade their lives a bit with someone they like.
The problem with needy SBs is that not only will they keep coming back with more requests.. they are more likely to drop you for the highest bidder.. they are looking at you as an ATM and not a daddy.

There are two scenarios to consider here:  
1. She asks for cash for something
2. You decide to send her cash (or a gift).  

 
Let's start with #2. If she's an ongoing SB, meaning I expect us to stay together for at least the next 3+ months, I have no problem occasionally sending a small gift when I see that it will be useful and appreciated.  Example: My 22-year-old Viet college grad (3 years as my SB) just bought a new condo with her mother. She moved in 4 days ago. Yesterday, instead of going out to party with friends for NYE, she was still unpacking boxes and trying to get organized. I sent her $75 so she could get dinner delivered for her and her mom.  I do things like this from time to time, maybe once or twice a month. I am confident that these gestures are appreciated. More importantly, she has never abused my generosity.  

 
Now on to #1. I make a point when starting a new arrangement of telling her I'm more interested in helping her with what she NEEDS, and less in what she WANTS.  Example: She may want a new Dior bag, but she only needs a new purse and something from Target or perhaps Macys will work. As long as an ongoing SB occasionally makes small asks for something she needs, I try to help with at least some of the cost. If she tells me she is $400 short on rent, I may only giver her $100-$200. Now if these start to get "abusive" I will start to reduce the amount I will send or will politely decline. How do I define "abusive"?  I don't have a set criteria. But if I find myself getting annoyed with her next ask, that's the start of abusive.  

 
One more dynamic is WHY she is asking. This circles back to the need vs want issue. If she texts me from a club and asks me for $50 to get drinks for her and her girls (that's a real-life example), I won't even reply.  If she texts me from the car repair shop to ask for $50 for a retread tire (also a real-life example, same SB), I'm usually going to send it. No doubt, she could be lying about the reason. But those lies usually become obvious over time and only push my annoyance level towards the abuse threshold.  

 
Considering the overall investment we make in Sugaring over a year, an additional few hundred bucks to ensure she stays happy and that she will return those gifts with "horizontal enthusiasm" seems like a reasonable use of funds to me.  

 
But like our intrepid Jedi Padawan, young Master Luke, we all need to use the force to determine if her asks come from the light side, or the dark side.  

 
May the Force be with you.

 
Life is good

 
The Cat

You are rewarding consistency.  Not being taken for granted.  My girls that are consistent get stuff like a dinner on me from time to time or grocery money if they are short.  

My main SB and I spent last night together.  We also did our Christmas.  She probably spent more on my gifts than I did on hers.  So, if she needs grocery money because her income is a bit inconsistent then she gets it.  

I had another girl who I've only seen a few times.  She keeps asking me for $100 all the time and I ignore her.  She hasn't put the effort in and already is asking for cash.

As others have said, never send money to someone you've never met.  And for the established SBs, occasional gifts like grocery shopping, a new battery for her car, help buying a computer, are all things I've done happily and seen as a worthwhile investment in a satisfying, ongoing arrangement.  However when a SB asks for money. I always frame my response as an advance on our next date. If she's ok with that, and if I think she's going to follow through on her end, then I'll send a few bucks.  The maximum will be up to the amount of her regular ppm allowance.  If she turns out to be the reliable, honest girl I think she is, then when we've had our makeup date, I'll still reward her with a half of her allowance for being an honorable woman.  If she flakes, I'm only out the price of one date.

are a basic part of the SB/SD relationship.  Once you agree on the ppm or allowance there should be regular unexpected gifts.  I often send my SBs an extra bit now and then for hair, nails, or just so.  Then they get nice gifts (or cash if they prefer) for their birthday, christmas, and our anniversaries.  I consider it an investment, also when I add up the hours they spend with me it's still much less than working girls.  And they so appreciate it.  Money well spent.

I agree with this and follow it for the most part. Most SB's are grateful for the gift, especially cash. There have been times when I've felt the gratitude was short lived but those SB's are now gone. Always better to be generous than withholding if she's been on good behavior consistently she deserves  unexpected gifts.

I have now allocated $600 for this year for miscellaneous expenses as it relates to SBs.  

 
Lets call it a petty cash for pussy fund.. LOL

I'm approaching the 2 year anniversary of my arrangement with my SB. I have stuck to our agreed amount throughout, never providing extras (and she hasn't asked for any.) I take her out and we even went to Coachella last year and she is up for travel so we have a caring relationship and get along great both in and out of the bedroom. Some months ago she was mentioning that doing her nails herself was stressful. It was just a casual comment, no expectations for me to do anything about it. I just let that sit with me for a while, then one meeting I said she should get her nails done professionally and I'll pick up the tab. She was thrilled. So she now lets me know when she is going to get her nails done and I send her the $ for it. (It's about every 2 weeks.) Afterwards she sends me pix and is always so grateful. I can tell it has made a big difference for her and has improved our relationship. Bottom line, it's often the little things. It works so much better when I initiate helping her rather than her having to ask.

Sounds like a very good investment. You effectively gave her a small raise and she appreciates it.  I might have presented it as a spontaneous gift: "Hey Babe, let me cover it for this time. I always appreciate what you do to look so good for me."  

 
The key words are "this time."  That may reduce the expectation that this is a permanent change, and it may help you later if (when) she tries to abuse your generosity with more "hints."  

If you don't keep these bound as occasional presents or treats, she may start loading up other costs that were never included in your allowance negotiations. Ex: "Daddy, I forgot to get cat food for Fluffy! Can you please set up a monthly cat food subscription on Amazon? That would free up more of my time for you!" (Yes, this, like most of my examples, is real life.)  

 
Life is good  

 
The Cat

How about gifts with a large measure self-interest involved?
I am thinking specifically about regular waxing, as in Brazilian waxing. Makes a huge difference as compared with simple shaving.

A 3 year SB of mine waxed, and it made a very positive change down there - paid for by her other SD

Those are the easiest gifts to justify. Like buying her favorite sex toys (like a Rose) or sexy cosplay outfits if she is into that. But keep those at your place, or at least not at HER place.  Helps reinforce how much she appreciates Daddy for more than cash.  A bit of Pavlov's Dog, you say? Ring the bell and watch her salivate. (Ok if you haven't studied behavioral science, you may need to Google this one.)

 
As for waxing, if another SD is paying and you get the value, that's the golden ticket, Bro!  

 
But one thought occurred to me as I read your post. Until I got to the last line, I wasn't sure if she was getting waxed, or you. LOL  

 
Have you considered getting this for you? Painful as hell, and in the US, not especially cheap. I haven't taken the plunge, so to speak. But I do keep things trimmed up with a manscaping electric razor. Once you have hacked back the overgrowth, it only takes a 5-minute touch up every 2 weeks to keep it clean.  Several SB's have told me they really appreciate my grooming. They, just like me, are never enthusiastic about climbing through a jungle to get to the pink parts.  

 
Life is good

 
The Cat

No. The warden would wonder what was going on.