The property's initial condition, though needing work, had strong bones, making it an ideal candidate for renovation.

I recommend Class A or B, not Class C if you're going to buy OOS and fly out to the areaAnytime a  turnkey provider, wholesaler, seller, agent etc that shows you a spreadsheet number with cash flow, appreciation, repairs, capital expenses etc those are ideal scenarios.

That said, if you've been a landlord for years and have niche relationships with contractors / roofers (or do the work yourself), then it would seem you're in the ideal position to make this decision. 

Ideally, he would roll the 2-3 million into a multifamily property to hold and cash flow from for retirement.

Honestly the suppliers I deal with dont like dealing with anyone but contractors . 

On an ideal Brrrr you extract all costs including the cost to purchase the property.  

I use both Propstream and pin 5 and neither are ideal for the New York, FL or Texas Markets.

You seem like an Ideal candidate to pick a househacking market anywhere in the U.S.

We have yet to have an investor who wants to put an airplane in their rental but niching down and designing for your ideal guest is certainly an approach that we take to help investors and host see success in their markets. 

When I had my property management company (and the people I sold it to and manage my properties continued it) the policy was late fees are split 50/50, which I think is the ideal scenario.My rational was it takes more time and effort as a PM to collect when a person isn't paying, and at the same time the owners might not receive the rent when they should, so 50/50 compensated us both.