I think it's more about how you carry yourself if you want to fit in at high-end places. While some wealthy people don't exactly dress the part, there are always some subtle clues to their wealth. It may as simple as an expensive watch paired with a shabby outfit, but it sadly often comes down to disregard for the hired help. I've spent a lot of time over the past few years watching other guests when I was at expensive hotels and for the most part, they pay very little attention to the hotel staff.
I've seen wealthy people pull up in front of a hotel and walk away from their cars without even being approached by a valet, or carry on a conversation on their phone thought the entire time they are are checking into a hotel, or step in font of a line of guests waiting to be seated and seat themselves at a table in the restaurant. While none of the above work well for us shoppers as ways to fit in, you can utilize the self-entitled attitude of many hotel goers to your advantage when performing required tasks:
-Ask directions to someplace in the hotel that's clearly marked, like how to get to the restroom when you are standing right by it.
-Ask a question of the staff that has already been addressed, like how late the pool is open right after they have told you the pool hours. (This one really gives the impression you are ignoring them)
-Ask for help in carrying even the smallest items to your room.
-Ask about the organic nature of all food products!
If you are hoping to became a hotel evaluator, also know that you can start out by taking assignments for individual hotel outlets before taking on an entire hotel. Take just the valet assignment to start with. Then a bar or restaurant...and then try to pair these things together by taking the valet assignment from one company and the bar/restaurant from another. Take the assignment that are just check-ins without the hotel stay, then move up to the one night stays. When you are comfortable with those, you can start moving up to the multi-night stays.
I always recommend taking local assignments to start with as well. Travel adds a lot of confusion to hotel assignments, so be sure you are totally comfortable with hotel assignments before boarding a flight to evaluate some place in a different time zone.