This thread does remind me of my two worst experiences. Once was a roach motel in Tallahassee. We walked in looking for a place to stay for a football game. We got to the room and as I sat down on my bed my buddy decided to check his bed (he was on the golf team in school so I guess he had his share of less than clean places) and he saw a non-descript bug running under his pillow. Sure enough, my bed had bugs too. We checked out right away.
Another was 2 years ago. I had to go to NYC at the last minute for business, and I have a thing about expensive hotels on my expense report (or used to) so I stayed at the Hotel Pennsylvania. I mean, it was right accross the street from Penn Station where I had to catch the train to Newburgh and such a recognizable name how bad could it be right?
While I enjoyed the experience of the building itself (huge lobby, architectural detail that no one cares to pay for anymore, etc). it was abundantly clear that the only thing they've been doing to this hotel since Don Draper stayed there in season 4 is vaccum it. I've never been so afraid of a hotel room in my life. It was a dark room, and while it was not obviously dirty, I can't tell you i felt confident touching anything there. I was glad to check out and not bring any visitors with me.