My husband and I have had the dream to own buy-and-hold properties and flips for years now but have never made any moves towards that goal.

I ask because you can turn this property into a short-term rental on platforms such as Airbnb/ VRBO.

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

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

@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.

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

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

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.

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.