@Bruised Pepper-When I travel, I love meeting people and kind of getting pampered. Almost like I am a different person all together on vacation. I usually go to just enjoy fine hotels, and also sight seeing.
I'd try to cure yourself of this attitude. My opinion? Staying at a youth hostel on Koh San Road in Bangkok will lead to far more encounters with interesting people and memorable experiences than staying at the Bangkok Four Seasons (where your primary interactions are going to be with the concierge and a sanitized tour agency). Doesn't mean you can't get a massage, but I've always viewed dropping $300/night on a hotel room the worst way to spend travel money.
I find that the more experienced you become with traveling, the less interested you become in luxuries, pampering and traditional sight seeing, and the more you become interested in "authentic" local experiences, genuine interactions (with both locals and fellow travelers), and generally immersing yourself in the "new" and different. That rarely happens in 5-star hotels which are designed to keep you in the dead center of your comfort zone.
I guess if you're making 6-figures and generally frugal otherwise, blowing some dough on a fancy beach get-away isn't the end of the world, but it's kind of the vacation equivalent of a $2,000 handbag. Nice, but ultimately unfulfilling.