I spent about a decade involved with a giant recreational community run by an HOA. The interesting part is that it was in a region with at least a hundred similar communities, and it was not only extremely well run, but it was run on dues that were half of what similar communities charged. When it comes to property owners, it was absolutely fascinating to see how totally divorced from reality a small minority were. One really common ploy was to "protest" by not paying dues at all, since you only owned an empty building lot, and therefore didn't use the communities amenities, so owed nothing. Apparently the million+ spent annually on everything from road improvements, to security, taxes on common areas, and liability insurance were "amenities" also, and why should you pay your share?
Then it came time for a special assessment. The state was was concerned about the condition of high risk dams, built on private property, and essentially said, if you are the owner of a significant body of water contained by a man-made dam, you will have to have it inspected and certified by a qualified engineer. Well, the huge dam holding back the 175 acre lake in the community, was in bad shape and needed major repairs. Once again, the HOA did a great job, and found a fund match government grant to cover half of the rebuilding costs, or roughly four million bucks. This left a special assessment of $1000 per property owner, payable in two yearly payments. As expected, this brought the idiots out in full force. There were arguments, ugly board meetings, and folks who refused to pay. Some of these dolts will be so bent on proving a point that they end up accumulating huge debts due to interest charges and fees, and end up turning a few hundred a year in payments into $5-10K messes. A small handful of them even end up losing properties to sheriff sales.
When it comes to special assessments of tens of thousands of dollars I can't even imagine. Good time to NOT be a board member.