Meaning the asset could lose 20% or so of its value before impacting our position.

If he meets all of the criteria what makes you inquire about his military status impacting him/her as a tenant?

The risk profile for someone who's a local GC and has worked on structural rehab buying a portfolio in a building is quite a bit different.Also, situations like this where professionals can properly evaluate risk and bring in capital to solve the problem of said older folks is a way to earn income and make a positive impact (assuming you're not low balling the distressed, fixed income seller).

I suggest you take a deep look at your community budget and determine the impact STRs have on your community.  

Question for our lending experts…If I sell my investment property “Subject To”, is my current debt on the property counted towards my DTI until my loan is paid off in full? Are there any ways to structure the purchase...

It doesn't not impact buyers as much from a tax perspective as it does the seller. 

DSCR loans have MANY variables that can impact eligibility and those variables all vary from lender to lender.

If you happen to be in a LIHTC area, then I do have an impact lender who might do a OTC loan, but it would be with limited recourse options.Non-Recourse options are very tough to find these days, even at banks. 

That mortgage will tie up your credit and your VA entitlement, impacting your ability to purchase other property.

Also, put any repairs pointed out by the inspector into the following categories (by priority)1) Health & Safety - to avoid tenant injury and potential lawsuits2) Property Preservation - to stop further costlier damages3) Government Required - city inspection repairs & S84) Marketing Negative Impact - who'll rent a house with purple bedrooms?