Had a set of tires once that sometimes took me days of trying to get on and off the rims. So tight that even without airing them up the spokes lost measurable tension. The one good thing that came from the accident that took out that bike, I don’t have to deal with those tires anymore.
As an on going thing, I generally really enjoy bike maintenance. But I will get frustrated on upgrade projects involving BB or cranks, to usually find there is yet another special tool I need. I don’t mind having to get one, I just hate that it delays the project.