He is a "holdover tenant," meaning he remains in the home beyond the term of his lease, but he still has legal rights. 

One cool thing that I recently discovered is the VA will allow you to use any remaining entitlement on the loan for a second purchase. 

I have been a passive remote landlord throughout the time, thanks to my agent and nice tenants over there.We have almost enough cash to pay off the remaining balances of the mortgages but obviously we want to use it in a different way.

Won't apply for everyone, but for those that are military and looking to turn your primary residence into a rental when you leave, you can keep the 4% assessment under certain conditions (remain on active duty and I believe it's limited to 1 property unless you advertise it for sale within 30 days of a purchase of a new house).  

This would increase the property’s value to about $608,000, and you could look at an 80% loan-to-value refinance, which should give you enough to cover most, if not all, of the remaining balance.This structure allows you to minimize upfront costs and take advantage of property appreciation over time.

This could be done through a "subject-to" deal, where the buyer takes over payments on your existing mortgage while you provide financing for the remaining balance.

National vacancy rates have remained flat in the first half of 2024, following a 90-basis-point increase last year, with major metro areas showing particular resilience.

This can result in increased depreciation deductions in the early years of ownership.Partial Disposition: When a component of a property is replaced or disposed of, you can take a partial disposition deduction for the remaining undepreciated basis of that component.

The early holders, who got educated, believed, and remained a strong hands through the volatility, will benefit massively. 

As long as you have remaining entitlement, the process is about the same.