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.

If you purchased a property, it is recommended to perform a cost segregation study prior to improving / rehabbing the property as it is harder to document after the fact.

How would people recommend approaching the initial set up of that property with an eventual exit (via sale or hand-off to PM/operator) in mind? 

If that is a stretch as to your qualifications, I would not recommend this as it would with relative quickness go to the attorneys to move forward with drafting, inspections, title search, etc.

Does anyone have any experience with a good program and can recommend one?

Whether it’s for fix-and-flips, rentals, or other projects, I’d love to learn more about who you’ve worked with and what your experience has been like.Do you have any solid connections or recommendations for private lenders who use their own capital?

We were using a 4th (not on your list) but I cannot recommend them. 

In most areas in San Diego, that is condos, town houses, etcWith that budget, I would be leery of recommending San Diego.

Account ClosedI recommend that have a consultation with your tax accountant and/or financial advisor on ways to reduce your taxes. 

@Stephen Keighery makes a point that it may not be a good time to sell, but I recommend you test the market.