Has the room ever been a smoking room?
Is there construction in the building or next door?
Do you allow pets? (if so, the place will fucking stink)
Crucial thing to do when first walking in the room :
Find the clock-radio and make sure the alarm isn't turned on for 3 AM.
Hotels are really one of those things where brand new is much better; I also realized that the quality of brand new hotels is actually a case of free added value. The room rate at a brand new hotel is not that much different than an old one - pricing in hotels is heavily driven by location and capacity, not room quality. With a chain like a Holiday Inn or whatever, it costs a lot to make a hotel, then it takes many years to make back that investment, and then after that it's pure gravy for a while, and then you gut it. During the gravy time, the old hotel is subsidizing development of new hotels. When you stay in a new hotel, you are being underwritten by people staying in old hotels.
There's a certain pressure to just not ask questions, come in, do what you're supposed to, book a room. Good people, players, alphas, they just smile and go right ahead and ask the question.