HOA in theory can remove free rider market failure if well managed, when there are costs and/or needs for management shared by all.HOA kind of philosophically touches on the oft debated (and oft oversimplified) ideological debate between centralization or decentralization of authorityMy thesis would be: I suspect that HOA developments have higher property values in general, however when controlled for development budget on a per home basis, I would wonder if this actually holds up over time.I have heard anecdotal stories of corruption within HOA bodies, and mismanagement. 

Like many have said, there are a lot of factors that have to be taken into account to properly answer that question.

Because when we moved out of our SC house our property taxes went from 4% to 6% so that ate into our monthly cashflow but had already accounted for that because we did our research beforehand so just another factor to keep in mind when looking. 

That is a very nasty loss.Upon further review there were several factors causing the neighborhood to drop in value.

My question to you all is how did you find and develop a relationship with your private money lender?

Conventional loans require as low as 5% down depending on your credit score and other factors.

If your intent right out of the gate is to develop and sell, the income wouldn't be short-term gain, it would be ordinary income with self-employment tax exposure.Holding for a year doesn't matter. 

Also seeing a lot of growth over in Decatur and the West side over their near the Bellwood Quarry development.

I loved going back and thinking about some past successes/failures, then breaking down, what was the product of my good or bad decisions, and what was due to external factors. 

Keep in mind the airbnb route will take up more of your time as well, which should be a factor.