Patrick, HOAs are a hard thing to manage. Its a classic tragedy of the commons scenario. Nobody wants to do the work but its almost always volunteer based. Even if property management is in place to manage it, they never really have skin in the game either. So what is to be done? You could throw up your hands and quit, but in my experience managing a high end condo complex HOA, I would build personal relationships with each of the owner/members and start to build a coalition of those who think similarly about things. As problems arise, they can be easily squashed because not only do you have voting power behind you, you also have the responsiveness of the owners because you have developed a personal relationship. This is the only way I see HOAs working well. As far as financial issues, special assessment in the short term, and run a healthier margin with dues in the future, making sure the property management company plays a fiduciary role and isn't getting ripped off for maintenance and contracts like landscaping. Hope this helps! Don't worry, everyone hates HOA management.