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.  

Source: WikipediaIncome persistence: You need a rental income that will last throughout your lifetime, which requires your tenants to remain employed at similar wages.

In contrast, any investment that requires management effort should yield much higher returns. 

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.

In contrast, maybe a great piece from @Bob Beach on how to avoid customer churn. https://www.biggerpockets.com/forums/899/topics/1175358-prop...Customer acquisition is only 1/2 the battle.

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. 

Next, figure out how much the entire rehab will cost and contrast it with the possible rental income.