Since the repairs were two owners ago, I would think the town may be a little more lenient with you.With the new kitchen and bathroom, were they existing and just got renovated or were they added on?

It may be best to partner with someone that has done one before or somehow is a local expert on lot splits.If you can add a bathroom into existing space on high cost property it can add a lot of value.  

I will also be doing all the cosmetic things you can think of: paint, flooring, bathroom reno, kitchen reno, so I am open to carpenter or design suggestions.  

I currently own a 2 Bedroom / 2 Bathroom Apartment.

FL has a ridiculous number of low-value properties, everything from essentially campers on 55+ lots to MH parks everywhere to run-down shacks in much of the rural areas, all of which is going to drag down the average premium.

As someone who did something very similar to this for the last 2 years - rented out my 2nd private bedroom and bathroom in my apartment (rental) furnished to traveling professionals and medical students - I think it's a great idea! 

Boots on the ground is hyperlocal, and what you're looking for is essentially cheap labor that can open a door when you need it.

Either way it would be a grey area, selling a house with a different amount of units/bedroom/bathroom seems extreme though. its an auction site, I have seen auction sites miss the fact there was additional lots in a sale.

Purchase price: $545,000 Cash invested: $545,000 New Construction Duplex - Beautiful Design and very nice curb appeal. 3 bedrooms 4 bathroom - All bedrooms have private bathrooms.

Additionally, I would like to attempt to do the process Owner/Builder with subcontracting work out as well as doing some of the work I'm comfortable with (I have some experience with bathroom & kitchen remodeling an am not new to the construction industry).