I'll go first. The most I ever paid an SB was about half that much and it was to my very first SB who was an ex hooker, but I got a LOT out of it.
We didn't really call it an SD/SB relationship, but that really what it was. I played Capt Save a Ho and rescued her from working for a pimp. I hired her to work for me doing light office work along with "benefits" of course. I paid her $300 a week to actually work for me, (which she kind of sucked at) and then to give her an incentive to fuck me, I gave her a $50 "bonus" for every time we had sex. She ended up making close to a grand a week out of the deal. She sucked at "work" but we seemed to fuck at least twice a day just about every single day. Even years later, we still call sex between us "having a bonus" lol We were on and off for about nine years and it's only been about a year since the last time I saw her at the ripe old age of 27. lol
In my "modern era" of SA I think the most I have given any single SB has been less than $2,000 during any given month. I did rent a car for one SB and gave her some cash from time to time on top of that, but I don't think we ever exceeded $2K.
So, how about the rest of you?
I'll just cite my max allowed and paid as long as I've been on SA (on/off) circa 2011:
A- Max overnight: $1K to this Ukrainian "goddess" (Z reference) or a TER 20+ (close to a 10 IRL at 5'10", 125 lb. blonde, like I said total goddess!) who had claimed all her past arrangements were in the 5K+ per month which was very plausible both based on her looks and enthusiasm. Of course I was almost 6 years younger then barely past my mid 40's so with the aid of some supplements, I really got my investment's worth with her. Never to be repeated, ever!
B- Max per month: $2.5K for one month arrangement with a 22 YO who was a legit 8 IRL. Lead to 4 BCDs and few lunch/dinner/beach dates. Lost her due to attrition to a richer guy from LA at 3.5K per month.
C- $600 was the highest ROB situation when I was duped and got flaked on. $300 another time when I just paid to get the b*tch outta my place without any p*ssy because I had made a terrible error of judgement in bringing her there in the first place!
Every thing else has been in the 1K-1.5k per month, $350-$500 per depending on the length of the date.
Ive had 3 ongoing. Probably gave one about 1200 in a month.
The most I've paid for a single date is $600 to an incredibly hot 18yo who insisted she would not do intimacy for any less.
The most I've paid for an overnight is just $400 with a long term SB I truly adored.
The biggest scammer I fell prey to is a hottie who convinced me to buy her a car that I've got over $4000 in and the promised dates have yet to be forthcoming. I learned a hard lesson with that one.