The following year, we started managing the proper FMR and lost none of the inherited tenants.

Will the authority reject me purely because they won't be able to properly background check me?

Sounds like you are only a few documents away from setting it up as a proper property management company.

Perhaps in the surrounding community, but not in St Pete proper.   

Don't forget to contact your insurance company - as breed/weight restrictions can vary from carrier to carrier.I usually suggest adding a section in the lease that is a notice to the tenant that the insurance on the property will NOT cover the tenant's personal belongings or their temporary housing in the event of a catastrophe.

Account Closed- You definitely need to know whether utilities are separated or not in order to evaluate the deal properly.  

It needs to cash flow properly to pay someone else to run it for you.Lastly, you could do all 3-4 things you have listed to maximize your learning curve. 

That's safer for you and if properly recorded is nearly as good for the buyer (depending on your state laws).

P.S If I posted this in wrong forum please move to proper one... ;)

My question is how should we structure this so that I'm properly compensated for the risk I'm taking?