I don't know if this is relevant or not to what you're saying. But. I am lucky enough that I have no worries about money, and get to have semi-regular travel around the USA and Canada. There have been a couple of times when I have made an offer to an escort where I would book a two bedroom unit, instead of just the one that I would need, and then offered the other room to an escort with no expectations. Just to support their business.
I've got my own things going on when I travel, and there is no need (or expectation) of any sort of 'service' fee. And, in general, I think outright kindness isn't believed or trusted, there's suspicion. It's made me not, for the most part, bother any more with making offers. And while it's annoying to see suspicion, when the only thing being offered is a kindness, I can also see that suspicion is probably a necessary and useful tool for the industry.