It's possible to make quite a nice living working F&B, a customer service job, in a tourist town. Don't just assume everyone working a role is beneath you and living some kind of shit existence.
Their are people making a nice living in every industry. The overwhelming majority of service workers do not.
There's a possibility that my middle-aged waitress is independently wealthy and just doing this for fun, that doesn't stop me from leaving a $100 at Christmas time.
It's not because I think I'm better than her, it's because in all likelihood, I've been just a bit luckier than her financialy.
This is exactly what people here are talking about. The $100 tip shouldn't have anything to do with you being luckier financially, it should be a gesture of appreciation. A $100 tip isn't a gesture of appreciation normally, it's a gesture of "I am more fortunate than you, but I take pity on you so here you are."
that's called projection. you surely would have come across that in all your pop psych and pop philosophy reading that you are obviously doing lately, right?