Home-Owners Associations: Vigilant or Vigilante?

I’ve never had the pleasure of owning a home, but it’s something I’ve been thinking about a lot more lately. I haven’t yet bought a place because I live in New York, where buying anything nice costs a million dollars, and also because I’ve been waiting for this housing bubble to burst so I can sweep in and buy whole subdivisions at a time for a leather bag of Dorito dust.

But after hearing the story of an internet acquaintance who got a knock from city inspectors for building a treehouse (the city said there was no code for treehouses, but his looked safe enough) and another friend who just got fined for having building materials in his backyard, the topic soon turned to Home Owner Associations. Neither of these guys got dinged by a HOA because their neighborhoods don’t have them, but it made me wonder if living in a HOA area would have allowed them to do either thing at all.

I can understand the appeal of a tidy lawn, but part of me writhes when I think about living in a neighborhood where I can’t keep my lawn long or my house painted in ridiculous colors if I choose. (My nightmare: the Michigan man who went to jail because his lawn had no grass.)

Rather than horrible HOA stories (HOArror?), though, I’d rather hear from you guys about positive experiences you might have had. What do HOA bring to the table that outweighs the lack of freedom you might have? And do you feel like having a HOA brings the majority of your neighbors together or that it frees you from having to interact with them at all?