In general, when you are self-employed (not a w2 enployee) and actively work in your business, you report the income and deduct allowed expenses on Schedule C.

For reference, I am self-employed (I run my own online clothing business, i am 1099-k) and I've always been told that it'll be hard for me to get a conventional mortgage when you're self employed, so I am specifically asking about other types of loan options.  

The employment GAP isn't always an issue as long as you're now a W2 employee, can show 30 days of pay stubs (not self employed), and you can provide a letter of explanation stating the cause of the employment gap.For a VA loan, in order to use the rental income from the other units you'll need:1.

Did you perform an actual employment verification?

Stronger economies generally support higher rental demand and property appreciation.Neighborhood Analysis:Safety and Crime Rates: Avoid neighborhoods with high crime rates, as these can affect property values and rental income.Property Demand: Look for areas with growing populations or proximity to employment centers to ensure consistent rental demand.Property Condition: For fix and flips or BRRR, assess the condition of properties carefully.

Based on your experience as a lender, what is my likelihood of having a "letter of intent to employ" accepted by an institution? 

We live in a bit of an expensive market with great growth, Navy, Shipyard, Medical, and easy commuting to a major city with a dozen or more major employers. 

@Carolyn Mazzola unless I'm missing something, appears you are confusing Property Management Software (PMS) with a Property Management Company (PMC).PMCs employ PMS to better manage properties & tenants.If you invest OOS, who will be your boots on the ground?

Once I plan to offer the unit, I offer it contingent on successful background check: In addition to the basic applicant approved transunion smart move through buildium which I pay for, when smart move stopped providing criminal background data, I  added a $49 tenant paid service through rentprep for nationwide criminal and eviction, bank account deposit verification, and employment verification.

Unfortunately my contract with my employer does not allow me to work for anyone else.