Real Estate, short-term management business groups in Miami and its surroundings ?

Maybe the answer is to hold the property but don't build the adu. 

Short of spending several years building experience with smaller deals, what would the folks on this board recommend?

@Nilusha Jayasinghe score system does NOT matter.What matters is understanding the risk of default any score represents.See link below for more info:https://newsroom.transunion.com/transunion-analysis-collecti...A landlord should ALWAYS get the SSN from tenants to protect themselves and hold tenants accountable.

Which one (usually, and I understand it's not simple) has a better resale and long-term potential?

Can I calm/deduct start-up cost for this property if i add it to an exciting LLC which already holds my first rental or what that expense be considered "operational cost".

Fannie/Freddie have more restrictions in terms of experience and net worth to qualify.

Bob is right that you can get better cash flow on the east side, but I still see deals pop up over there from time to time and I don't see any rapid depreciation in those neighborhoods coming any time soon and I think if your strategy is to buy and hold in nicer areas with less risk, it's a very good area to target.

You can also usually get a conventional loan with more favorable terms if you are living in the unit for at least a year. 

I have a background in freight transportation as well and actually lived in Toledo for a short time.