Well Tour, I do believe that one of the Junkies who responded to your questions, one who has done a lot of OTC with a fairly high number of strippers, gave you this piece of advice:
"...In any event, the best way to avoid confusion is to be as clear as possible as to what you are offering and what you expect for it. Trust me when I say you are not going to shock most of these older guys by laying it out, lol."
Avoidance of ambiguity and confusion was precisely why he said this to you, but instead you decided that the only takeaway was some vague notion about each person handles it differently. I hate to be the type of guy who said "I told you so", but... 
IMHO, you really need to make it clear, long before the meetup, that this is a pay date. Some girls will say it bluntly, but some tapdance around it. I cannot count how many times I've had a dancer say something like this: "I'm really looking forward to meeting up with you, but I really do need to earn something if I'm not going into the club that night. Would that be ok?" At that point I propose a number or she does. The benefit of letting him do it is that he may come in higher than what you were going to quote! But if he does come in too low, or doesn't propose a number at all, you can always respond with something like "would $xxx be ok?"
As I said before, he shouldn't be remotely surprised. And if he is surprised that you asked for money, then the meetup was not going to go well for you anyway and you just saved yourself a lot of grief.
As far as your other comments...
- The club is precisely where most girls work out the terms of an OTC meetup. This actually makes the most sense, since you are in person, your roles are clear (dancer and customer) and he should be in the right frame of mind.
- In terms of the "experience", IMHO you should let him drive the bus. If he wants to take you to dinner, let him choose the place. If he wants to take you to some other entertainment event, tell him to surprise you. If he just wants to take you to a hotel room, then let him choose the place and make the arrangements. Just be mindful of your safety. Beyond that, the only things you really should have to worry about are looking good, being an entertaining companion, and, finally, number 3 below...
- Irrespective of his money and charm, he is just a man with a penis who wants to get into the pants of an attractive woman. Trust me when I say that there is no need to over-think his expectations and desires. Whether he wants to wine and dine you first or go right for the gusto, make no mistake that his end goal is the same - to separate you from your panties. And, once the panties are gone, the rest is like riding a bike, no?

Anyway, just my
for whatever it is actually worth and good luck!
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