At the risk of offending everybody on all sides, let me take a stab at finding some middle ground.
Gopher, although Zig didn't exactly ask for any advice, the title he chose for this thread "Right or Wrong" kinda suggests he was asking for opinions. Perhaps he was really just looking for reassurance (which he got plenty of), but since he also characterized his post as a "Confession" and his actions as "rationalizations" he had to at least have expected the usual moans and groans and "ya should never have done thats". To then react so strongly not just to Coqui, whom he should REALLY have expected such a response, but also to SubAtomic, for which he was advised to chill by the admin, well, lets just say this is a public board with a wide range of members. So if you can't take a few negative comments you should just save your sharing over a few Imperials at the BM happy hour with a more carefully selected group of friends.
Coqui, I know you have opinions on everything (so do I

), but just in case you haven't figured it out yet, you rub a lot of people the wrong way here so you should be more careful how you express them or whether to refrain from comment altogether. Zig is right, given your relative lack of experience with TICAS, you're hardly the best person to contradict what nearly everyone else hear is saying.
You also seem to have failed to recognize several important differences between this case and the typical chica-dinero situation most of us have faced. The girl didn't actually ask for money, it was offered. As far as Zig knows, and we have to defer to his instincts on this, she is not a pro that has made a habit of getting money from gringos, at least not yet. The amount of money, again at least at this point, is fairly limited. And Zig is not some gullible newbie. Presumably he has seen manipulating chicas before and knows to watch out for them. He knows the various probabilities of attempting to do what he is, and is willing to at least risk the relatively small sum that he has laid out for now because he knows it will make him feel good if he succeeds. Actually, whether he succeeds or not, he figures it was worth a shot (like a roll of the dice) and he will be able to feel good that at least he tried.
Sure this case is a little different, but is he right or wrong? I'm not expert enough to say. Probably only time will tell. But at this point, Zig is probably in the best position to guess, assuming he stays at least partially grounded and is not blinded by love or lust (or it seems has his rational thought processes fogged by too much alcohol).
Personally, though I don't know the girl, my less-educated prediction would be more pessimistic. I don't think she was playing him. After all, the money seemed to be Zigs idea not hers. But was she deliberately hinting for it, hoping he'd offer

? Giving her the benefit of the doubt (and trusting Zig's instinct) that she didn't initially expect money from him, now that she realizes he is a potential source of bail money, will she go to that well again? There is definitely a good chance. $100 is nothing more than a small stopgap measure. Unless she finds that "civilian" job that she's failed to do up until now, she'll soon be forced to either hit Zig up for more cash or seriously consider giving the BM a try (or maybe both). Unless one is prepared to go all the way in underwriting a girl so she doesn't have to do that, partial measures are probably going to be just like pissing in the wind.
Oh yeah and in answer to Bombero's question "If it made you feel good doing it, how can it be wrong?" Tequilla make you feel good at night, but makes you feel like shit the next morning. Thats how it can be wrong. Zig feels good now (though he does seem to be having some 2nd thoughts). Hopefully he won't feel too bad if it turns out his modest investment doesn't pay off. But if it doesn't and he falls into the trap of throwing more good money after bad, he could end up with something much worse than a bad hangover. He could end up with a broken heart and a depleted wallet. Hopefully, he has enough sense and experience for it not to come to that. But just in case, perhaps, next time he talks to this chica he should lay off the "tequilla" or whatever his poison happens to be, since that was partially what got him started down this road to begin with.