Do this before you decide what must be included in a Rehab budget and what can be deferred as part of your CapEx reserves requirement.  

You are basically trying to finance a deal that is destined to fail.

I would personally pick option C.Place tenant myself and self manage for the following reasons:I don't like giving away 10% of my rents.No one is going to care about my property more than me.I have systems in place that allow my to self manage with minimal time.I have a great support staff that I can text when there is a repair that is needed.I rarely take calls from tenants and tell them to text me to keep from getting caught up in their drama.If they don't pay rent on time and it is a repetitive problem I file an eviction to train them they must pay on time or go somewhere else.They can pay rent with Zelle, paypal or deposit rent into my bank account (most deposit into my account)It is their job to pay rent on time I do not collect or chase rent it comes to me.My rental portfolio is very passive with little interaction required by me.

Here is my question to those who have experience in purchasing a property under these conditions - if a city performs an inspection prior to the house being listed and it fails, is an investor able to buy the property prior to repairs being performed with the understanding that these issues must be repaired so it can pass the inspection before selling it to an actual homeowner?

One element of adverse possession in FL is anyone who tries to make such a claim must have paid the taxes.What was the point in getting a survey if nothing was going to be done about any problems shown? 

If it's a standard Lakewood up/down duplex it probably has a plaster ceiling under the ceiling tile-- at least all the ones I visited when my son was apartment hunting were plaster.IMO, the "nicest" fix (assuming the old plaster is in poor condition) is to scrape off the acoustic  tiles and then drywall over the old plaster with a smooth finish; the cheapest fix, if the only problem is the one tile you pictured, will be to screw up the tile(s) that is/are lose, cover the screw with a little joint compound and then primer and paint the ceiling; If you are lucky the tiles have already been painted before.

To live there it must be his primary residence.

It must have fire extinguishers, emergency lights, ext.  

For the buildings requirements I just cannot have anyone stay for under a month, and they must abide by all the buildings posted rules or I am charged with a fine and responsible for getting them out.

I think that's because my focus is Class A or Class B tenants (minimum 650 credit scores and verified income must be at least 3 times the rent) - easy tenants.