A large percentage of investment RE owners pay little to no tax on the money they're earning in RE.

The question is, what date is used to qualify the year of holding to avoid short term capital gains tax?

@Patrick Fricchione, You will not create any tax consequences simply by converting the use of a property. 

Private money funded the $90k down payment at 8% interest, no payments due on that until the balloon in 48-months.

We have a lot of money tied up in the unit and would like to find a rental unit the we would consider living in at some point with a house hack option/ADU and or a home that has a better long term appreciation potential. 

If you could renovate and split off an ADU or even apply to turn it into a duplex or triplex (although that will cost plenty of money with new kitchens, utilities, etc.) that could very well be worth it.

Whether it is loud music at night, or "Hey, our car broke down and we won't have all the money this month to pay the rent" - how you handle those situations.  

Contacted the Housing Authority to confirm if I were to receive or deny money being that the security deposit was covered.7. agreed upon moving forward, May 14 an emergency happens & couldn't meet for the keyThe housing authority are very hard to contact for answers and the case worker for this case is on vacation this week.

They are "okay" for generalized information, but if you are putting money on a property, in my opinion you want better analysis than those provide. 

If you just sold the property after building equity then put that money in the S&P 500 you make way more money.