He is nearing retirement. 

Hoping that cash flow will improve substantially as this is going to be a big part of my retirement.

This are the best few hundreds of EURs you will invest and can save you thousands.On my case, i'm currently in the process of investing in 2 properties in Sagres for tourism, as the zone belongs to a natural reserve and supply is very limited (i also hired the 2 ppl i mentioned above).

How we purchased our property: Combination of Savings, Personal Loan with interest from a family member (4% interest) and a cash loan from Wells at about 8%.

I'm from Leesburg, an active-duty Air Force member, too (retiring soon).

If not get yourself an agent who can represent you and save you some time along the way.

For yourself, I'd save up enough to be able to house hack, and then house hack.Hope that helps.  

You don't have to be a contractor but it will save you a good chunk of money. 

If you discovered the issue before paying for the appraisal that could hopefully save some costs (in case the appraiser is with the wrong AMC).Pre-vetting with the lender on rental history/AIRbnb/1007 as well as seasoning could help. 

You literally have to invest in something that will lose value, in the hopes of saving on taxes."