Right around that same time, my dad had his vintage airstream returned to him after a breakup. 

I had a business partner "break-up" involving a house many years ago, so I kinda relate.As to your questions:1) (a) Based on what you wrote - purchase price $260k + $50k in renovations, and possible current value between $260-$290k.

Wherever you have vegetation or things that break up the falling water, and/or the water flows AWAY from the foundation, doesn't pool, it's usually fine.

We can break up the vacant doctors' offices by turning them into smaller suites, and charge a minimum of $15/sq.ft.

We can break up the vacant doctors' offices by turning them into smaller suites, and charge a minimum of $15/sq.ft.

We can break up the vacant doctors' offices by turning them into smaller suites, and charge a minimum of $15/sq.ft.

You're looking for possible repairs whether expensed (like dumpy apts needing rehab on a turn) or CapEx (roof has <5 years, siding has moisture invasion, leaky plumbing, paving is starting to break up). 

The main difference I see with tenants in this kind of area is that they are rarely able to cope with a major setback - job loss, relationship breakup, unexpected family addition.

Also, break up the renovation project into phases, not just one solid lump sum.

Hey @Shawn Gardner - That can get quite pricey if you don't already have underground utilities that are existing because then you have to break up concrete to install new drain lines.In Chicago, for a typical bathroom, we are usually in the $5-10k range but that wouldn't include any of that underground work.