It doesn't sound crass to me. Not at all. I agree with you. Over the years I have heard so many hard luck stories that I've lost count. Maybe some of those stories were true, but I believe most were bullshit, just trying to get money out of me. And if I ended up losing a boy I liked because I refused to give him money, that never bothered me. Plenty more where he came from. The way I see it, if you can't be, or won't be, honest with me, as far as I'm concerned it's no loss. And I'm not about to let myself be put in a position of having to decide whether the story is honest or not. For me, it has become very simple. My answer is NO.
I don't fall for those stories anymore. Haven't fallen for them for years. First, I don't let these boys turn their problems into becoming my problems. Unless it is someone I know very well, for a long time, and am absolutely sure I can trust, when I get one of these stories my response is usually something like "Sorry to hear that" - and nothing more. They don't get money out of me. As far as I can tell, they have all managed to survive without my money.
And if that sounds crass, too bad. Fine with me. I gave up being the naive farang long ago - and it's going to stay that way.