Your federal tax bill on $250K of LT capital gains is probably relatively modest.

They probably have incentives for owner/occupants

If I do sell years from now I would probably just 1031 the property. 

One tangential thing that maybe is missed or isn't clear from the above discussions, you will probably not be able to shift from long-term to short-term during the year AND use the "average rental interval of seven days or less" way to categorize the income or loss as nonpassive.Example: You rent for month of January as "long-term" rental and then do weekly rentals for the remaining 48 weeks.

I was looking for more of a sense of probability of completion to purchase, since most people I know who do L/Os don't do much volume --so the stories are more anecdotal.

I know that's not the principal of house hacking but that's probably what you'll find.

Sorry.Investors for sure (and probably some promoters) regularly fail to consider a bunch of issues...1.

Probably needs a new roof within 2 years so that's on top...  

I used to host a free  weekly session that taught people how underwrite multifamily deals, so I can probably give you some pointers.

You need to be in the borrowing LLC to get the experience and probably to be safe own 20% and then you will get credit.