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.

And I'll bet the market is very workable... you're going to do great there. 

Having multiple exit strategies makes your investing a lot safer and more liquid.

Your best bet would be to find an owner that is open to seller carry.

I feel that my money would go further and be safer splitting a property with him (helping him as well) than in my inflated market.So i guess in general with this post, I'm hoping to hear from anyone who has experience in the area, specific areas to invest in, connections with investor friendly RE agents/contractors/property managers, anything will help.