Walking through, I can see that owner is the type that spares little expense with his own properties. 

I can go way deeper into finding good MTR markets, pursing tenants other than travel nurses, property types, scaling operations through systems (my specialty), renovations, etc but it's much harder to do in a thread.

General Contractor - Look for someone experienced in renovating older structures common in Baltimore.

Now consider this: all the groups people are spending fortunes to target—foreclosures, absentee owners, probate leads, tax liens—what do they have in common?

If you want to be active, you will get a lot of good advice on this Forum about what market to invest in and what type of active property. 

But it doesn't seem to be riskier and more doomed to fail than BRRRR and other types of long term holding/land lording.  

Duplexes are very common here and are much easier to find than a Quad as well.

Has anyone been in a similar position, or has had success offering this type of agreement to a previous owner of a property who has not yet voluntarily vacated?

Rising land prices are not that common either, and limited to select areas.  

Would love to hear any experiences with this type of strategy