Then a Civil Engineer, an Appraiser to determine what having a four unit would be worth, then a loan using the evaluation.

@Jason Tucker  you need to add in your utilities, common area cleaning, and turnover costs to determine if it makes sense. 

Because they aren't traditional tenants in the sense with a 1 year lease and to determine fit for the house, I like to start everyone on 2-4 month leases and see how they perform.

I think the ability for the lower cost places in the midwest to 'cash flow' has been way, way overstated.If you know a market well though, that's definitely an advantage.

The location being Las Cruces, New Mexico was yet another sucker punch that has negatively impacted my ability to do much with the property.

This is because VA loans are tied to the borrower’s personal ability to repay and require a creditworthiness review.VA Entitlement Consideration: If you’re assuming a VA loan, the original borrower’s VA entitlement may remain tied to the loan unless you’re a veteran eligible to substitute your own entitlement.2.

Getting your real estate license can be helpful, especially if you want direct access to listings, market data, and the ability to save on agent commissions.

What’s the best way to determine if a lender specializes in conventional, commercial, hard money, non-QM, or DSCR loans?

If your numbers are solid, you might even be able to cover the monthly payments out of the rehab budget.This kind of setup works best for properties that need significant rehab, and you need to be confident in your numbers and your ability to get the work done. 

You can't raise the rents in a fixed term lease but if it's month to month you may have the ability to make a change with notice (30 days is fair in my market).