Just a quick trip share here. Recently, I went to Louisville and stayed at the Omni downtown. They have a rooftop pool and hot tub. Sadly, there was a fair amount of rain, but I still got to lay out for a bit and spend time in the hot tub, only in thongs. The pool area wasn’t super crowded, but still pretty occupied, except for the first day which was a crazy madhouse of children for a sports tournament! No complaints at all, at least not about swimwear, although people seemed upset about 10-year-old kids doing cannonballs in the hot tub!
Went to the same hotel last year, during warmer weather, and spent much more time on the pool deck. At that point it was very crowded, basically every lounge chair was occupied and only a couple of feet apart. Even then, laid out, spent time in the pool and hot tub and had no issues at all.
Probably more a testament of the importance of being confident and not being creepy rather than what it might say about the area or the hotel.