My ex-wife’s condo HOA had a huge grass berm that was overgrown. They ended up hiring a guy with a flock of goats to eat it down. It became an event to watch them and was the most popular thing they’ve ever done.
As for a nightmare story. Me good friend’s brother-in-law is a complete fuck up moron. He inherited a very nice house that was part of an HOA no one wanted to run it so he volunteered. Everyone agreed because they hadn’t yet realized that he was an idiot.
He convinced the group to pay for a giant stone pizza oven in the common area. To save money he built it himself. It is a huge monstrosity. He didn’t get a permit. When the authorities got wind of it they told him that it was illegal to run the thing and that there was no way to legally retrofit it. No one wanted to spend the considerable amount of additional money that it would take to demolish the thing so it still stands as a monument to him and people have to see the thing every day.