There is no hard grading system on investment properties so “Class D” would be a subjective term but ideally it would refer to the “state/condition” of the property, “quality/affordability” of the tenant base and the “rent/income” it could provide.  

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.

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

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

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.

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.