This decision often comes down to a simple numbers game.

My end game is to show you a path to financial independence, whether that be at 45 yrs old or 70 yr old.  

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.

They used that period of unemployment to skip paying student loans and then try to get some kind of program/hardship deferral or something aka "gaming the system".

Quote from @Aaron Letzeiser: Quote from @Mohit Gupta: @Steven Toth I was actually able to find multiple carriers who would insure for a slightly higher premium, which I am happy to pay.

If appreciation is not there, however, it seems like a potentially long waiting game to see if your $60k investment today returns anything meaningful in the long run. 

Commercial is a totally different ball game than residential, so connecting with a commercial broker will definitely make your life easier.

I'm sure y'all already knew that!

Focus on what the rents will look like post-renovation with 4 units instead of 2, and have a clear game plan for refinancing to pull your capital back out. 

Hey @Marc Shin, so yes on the games.