I put a new build under contract early this month, and are now working on the loan with a credit union.

Your background as a military pilot.  

@Ryanchase Balthazar  That's how I got started, in the military. 

If you are running a LLC for your rentals is essential that you keep all business  funds in a separate account I like Credit  unions the best .

If I were in your position, I would look for a bank or credit union that will give you a line of credit against the rental property.

Moreover, "[v]olitional unwillingness, as distinguished from good faith inability, to meet contractual obligations furnishes neither a ground for cancellation of the contract nor a defense against its specific performance" (Meisels v 1295 Union Equities Corp., 306 AD2d 144, 145 [2003]).  

Being a military member house hacking is the easiest way but I’m also open to learning new methods and if at all possible learning from others’ mistakes. 

Are there specific military programs or contacts I should look into for housing opportunities?

Make sure to consult a financial advisor if necessary and also consider reaching out to your local credit unions.

As someone with a military background, I’ve always approached investing like a mission—know your strengths, assess the terrain, and execute strategically.For me, starting with SFHs felt like the “crawl” phase before running into multifamily.