I'm a central CT based investor, flipper, and property management company owner. 

I’m also based here and have experience with short-term rentals, property management, and work with investors like yourself.

Money makes you happy only so often.But a good place to work keeps you happy every day you show up.Yes, 𝗺𝗼𝗻𝗲𝘆 plays a vital role.But 𝘸𝘩𝘦𝘳𝘦 you work?

However, this is not specific legal advice to you, just an opinion based on the circumstances described in this thread.  

When you go to sell, Montvale requires a certificate of occupancy so this issue has to be resolved in advance of a sale.Although I am not a lender, I assume you will not be approved for an owner-occupied mortgage on 5-units if it is a legal 4-unit without some type of mortgage fraud whether in reported rents, units, or another legal document or representation (very very large issue from a legal perspective with multiple arrests in the last year for anyone playing fast and loose).As far as the DCA, I would recommend coordinating your work with the city with the DCA.

However, this is not specific legal advice to you, just an opinion based on the circumstances described.  

I am based in NOLA and have a great property manager.

It's all relative and subject to change based on each individual person.

There are two options I have offered and I want to get a check on here if I am off base with my offer or if I need to push harder.

I would only consider Decatur for a cash flow play, not an appreciation play.