Your background as a military pilot.  

You make the payments to the lender.Oh, and just in case, there are more items to know about when considering a "sub to" transaction but this is just a comment on the payment aspect. 

Certain cap items is fixed or pretty close to fixed whether you are buying a $60K house vs. a $500K house in the same market. 

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

I haven't filed a claim all these years but insurance is for the what-if and to be used for the high-ticker items, but chances of damages exceeding the 5% is low.  

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. 

I would only recommend purchasing items that fall into that vision. 

Look at insurance and tax costs, those two items are the biggest killer of cash flow.

At the end i will add a list of items why adding a single ADU in single family zoned areas may not be the best RE option.The most common value add is via a rehab.  

This could be an opportunity to add value by offering to help with clearing or relocating those items as part of any potential agreement.Why This Could Be a Good Move for YouYou see long-term potential in the property, especially with the large lot and development possibilities (even if those are years down the line).As the current tenants, you have the advantage of a direct relationship with the landlord and familiarity with the property, reducing competition and risk.This could be a chance to lock in a property that you might otherwise lose if it hit the open market, especially in today’s competitive environment.Challenges to ConsiderIf the landlord is emotionally tied to the property or reliant on rental income, they may be reluctant to sell.Financing could be tricky, especially with today’s interest rates and the gap between the current rent and what a conventional loan might cost.The development potential you’re interested in is likely a long-term play, which means the property could be financially tight in the short term, especially if you’re only breaking even or slightly negative on cash flow.Structuring a Potential DealTo make this feasible, you’ll likely need to explore creative financing options that align with both your financial capacity and the landlord’s goals.Seller Financing: Propose a deal where the landlord acts as the lender, allowing you to make monthly payments directly to them.