HOA Horror story..
A smaller community, 20 units, trusted one lady and had her in charge of the HOA. She'd been doing it for years and years with no issue, and nobody thought twice about re-electing her. Well, she passed away, and two new board members took over. Turns out the original lady had been stealing money from HOA accounts for personal use (no oversight)! Their reserves were completely gone, she didn't have records of who paid their dues, she let the insurance on the building lapse, etc., and she died with little to no estate for them to try and collect from.
Everyone who lives there had to pitch in quite a bit of money to get the insurance going again, and their dues were raised significantly to build reserves and take care of neglected maintenance. And NONE OF THE RESIDENTS HAD ANY IDEA! Shit, if there was a fire.. I can't fathom how the residents would have come up with the money for repairs.