Never had to deal with a home owner's association directly though I can imagine what a pain they might be. It really depends on the HOA, the neighborhood, and the issues in question.
I've worked for an HOA, not as any official member but more as one of their maintenance people. However we worked as handy folks for a few of those (very wealthy) residents first. This one was actually rather easy going so I consider myself lucky. However I have seen some which throw a hissy fit if the housekeepers or guests so much as park the least bit out onto the sude if the road.
That's right, Bixby Snyder folks.