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.

Last year, on my 9 properties I had negative cash flow after accounting for mortgage payments, etc.

Once you graduate and have a steady income, consider house hacking as a beginner-friendly strategy—buying a small multifamily property, living in one unit, and renting out the others to offset your mortgage.

We wanted additional units to pay mortgage and have cash flow.

If you’re making a return higher than a bank CD you can support a mortgage.

I taught myself Spanish, I already know the construction crews in the area, the realtors, the communities, the land, I have someone managing the property, I have a maintenance crew… I already did an incredible amount of the work involved in finding a deal and turning it around through reconstruction and proper management.

Private mortgage insurance i believe is not charged on va loans.  

that we’ve learned in our 24 years, managing almost 700 doors across the Metro Detroit area, including almost 100 S8 leases:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

Can anyone recommend software which would accept monthly payments (from me to seller) and create proper 1099 forms for tax purposes at year end? 

Another option is to invest in the market instead of paying down a mortgage.