Maybe I'm a sucker, but forget that property.

Best bet is to become friends with other local owners.

I I chose R-20 as I felt that was safest bet considering I couldn't live on the property otherwise and it would put the originally staircase in jeopardy.

Having an additional 10%-15% of your rehab budget for cost over runs is always a safe bet, and then there is the monthly carrying costs.  

Buying your own home will reduce your taxable income(a benefit in the now,) and will give you a more certain understanding of future housing expenses, and may even give you and your family a sense of security, but in order to be a better bet financially vs. renting, you practically need a high level of appreciation.  

I bet if you focused 100% of your efforts in Lauderhill FL, you would be able to get a few under contract.

Your best bet is to go there on an evening and see how the block looks then. in a way you are fortunate because these are the summer months and you can get a good feel of what goes on around that house. if you see a lot of hanging around on porches or a house with a lot of traffic (foot and car), proceed with caution.  

So maybe the insurance policy is a better bet for me?

Depending on the zoning of your property, the configuration of your lot and the construction of the garage, you may not be able to get a CO from your city for the extra unit.Your best bet may be to make use of the space yourself, provided that your tenants still have proper parking.

Best bet if he/she wants to stay they must sign the lease or leave the property.