Ten years ago I was a single mom, newly divorced and getting to the world on a VERY tight budget. I spent enormous amounts of time and energy getting the best deal. Then, I had more time than money.
Fast forward 10 years, I have my own little consulting business, I'm remarried, things are going well - I'm not rich but things are OK. BUT, because I consult, my time is often worth MORE than my money. If I spend two days getting a $500 discount, believe me I lost more than $500 in fees. I will be ahead more money if I book the higher priced room, rent a car (again, a timesaver) and get back to work. Now I'm not SILLY about it. I wouldn't do $700 for a room, but I can understand for a suite, especially if this a very important vacation.
I didn't feel poor back then, and I don't feel particularly rich now.
It's all in what works for you.