If you do end up staying for a total of 2 years in it as your personal residence and then sell it, you can keep all your profit tax free (its up to 250 for an individual 500 couple but you already stated your profit margin) 5.

When board members go rogue they open up the HOA to legal action and if their violation is egregious enough then their Errors & Omissions insurance may not cover and they can be sued as individuals.

I consistently hear that the rich tax savvy individuals buy property and equipment in the businesses name.

Travis,How well do you know this individual? 

In other words, the individual wants to purchase an STR but doesn't want to manage it at all.  

To make sure I understand, it's for people who don't have a lot of time during standard working hours or individuals looking to test a market.

CONS: HOA fees can be hefty, you can be individually assessed if there is a large repair in the complex and they don't have the money in the budget to repair. 

Read lots of books, listen to tons of podcasts, read blogs & forums, go to your local Real Estate Investor groups, network with other like-minded individuals, find a mentor, and don't over-analyze.

Check the SDAT info to see if the sales are to individuals or corporations for any clues, such as are the transfers to individuals with the same last names, are the transfers between financial entities, etc.

The percentage of the self rehab is really going to be dependent on the individual, and the capacity at which they can handle the more difficult jobs (electrical, specific carpentry work, etc.).