In either case, all of the income and expenses will need to flow in and out of the retirement account.4.

The rental income is their retirement income.

How long before you'd like to be semi-retired?

While not as stable and predictable as the military rental market, there is opportunity there.

I worked as a handyman for the owner and he was looking to shed his SFH's and retire to Georgia.

I had a great agent there but he has since retired.

I think our initial thought was to refinance to have the cash available to buy 1-2 more, and hopefully down the road have 5 paid for by retirement age long term.

I know this because I just retired in June 2019 with 23 years in Army National Guard, and while I didn't do what you're doing I know the lingo.I am not a fan of leaving a trail of rental houses dotted all over the CONUS. 

He is a man of his word and was grateful for his work however he has since retired!

I did martial arts in San Diego for a long time but was long "retired" (a little early due to a knee reconstruction) by the time of your injury and did not hear about it.