I apologize for making this longer than it probably should be, but I wanted to give you all a proper background and my vision for the future.

This could impact a future buyer, in fact I just had a buyer go under contract and we later found out that the proper permits were not pulled on work that was done to the property.

Yes, you need to refinance to pay it off and that means you will need to establish equity based on a future appraisal, not your old sale price, you need to have a conversation with your lenders before hand to ensure you can meet the future obligation.

You do not need to record the survey.. just have him locate existing pins.. then eyeball it for yourself.You can also ask for an Alta title insurance policy and that will ensure you for enchroachments etc.

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.   

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.