I’m not on the level of mike710 but close when it comes to number of stays.
Book my own hotels when traveling for work and for work or personal I never book below a 3.5 star hotel unless I have no other choice. For reference the max is 5 star and even most large cities have nothing higher than a 4 star. Many small to midsize cities have nothing higher than 3.5 star, sometimes 3 star is the max. Priceline and Hotwire have saved me tens of thousands of dollars over the years. I’ve stayed at many great hotels and years ago sometimes I only paid $65 but those days seems to be long gone.
Of course I’ve stayed in a 4 star that shouldn’t be a 4 star or a 3 that shouldn’t be a 3 etc. When in doubt I go to trip advisor which has often helped me avoid the crappy double tree and helped me choose the nice embassy suites instead which is down the road (as an example).
Three bad ones that come to mind are once I got a flight cancelled at 10:30 at night and they put me on the next flight at 5:00am. I made them give me a nearby hotel and it was a Microtel. Place was so shitty I slept on top of the bed cover with my clothes and shoes on.
Another time I was working in a small very bad city and stayed at what I thought was an okay no-tell motel. There was a lot of noise in the parking lot at night, every time I looked out there’s be two parked cars and people talking. Didn’t think much about it. Next day when I went to the business I was dealing with they asked me where I was staying and I told them and they flipped out saying 2 people were murdered there last week and one OD’d in one of the rooms. I then realized those were probably drug deals going on in the parking lot all night.
I once passed out at the Palace Station in Vegas (bought the room at 7am) after a long night at Sapphires and my buddy who lived in Vegas said “go there it will be cheaper than a cab to my house and I’ll pick you up at noon.” I had picked up a stripper with me and we were so tired we just fell asleep.” The room was horrible but oddly enough it has this nice freshly remodeled bathroom. My buddy picked me up, we dropped the stripper off at a Wendy’s and went to a pool party (we couldn’t drop her off at her boyfriends house who she was living with). That night the stripper agreed to meet me again at the room (so I actually went back since technically I checked in the same day) but she was a no show so I spent another entire night in the same shitty room by myself waiting for her. Turns out police were scanning the parking lot license plates at Sapphires that night and were giving her a hard time since she was driving her boyfriends car who had a warrant that she claims she didn’t know about. She said she actually took a cab to the Palace Station but couldn’t ask them to call my room since she couldn’t remember my last name (which I never gave her) and the room number I had txtd her and when she went to plug in her dead cellphone into an outlet to call me security came and harassed her (probably thinking she was a hooker) she got scared and left. That story could be all bullshit but I believed her because I went back to Vegas a month later and had a long , wonderful relationship with her, and crazy stuff like that always happened to this girl - just like many other strippers we all know as well.
My favorite hotel of all time (based on the hotel itself and not its location) Henry Autograph in Detroit. Right down the road from the Flight Club.