He’s like her to stay, but understands that the market rents are much higher.I’m wondering your thoughts on how to structure a deal to keep her in the unit at a slightly higher rent, but push for a discount on the asking price.Any ideas of an innovative strategy that could be a win-win?

Dont be an Idiot , matter of fact if he has keys , change the locks , put his tools outside and tell him to get them . he could squat and clain that living there was your arrangement .This guy does have a Mbs and a Phd .  

But giving them to option to fix them verses giving you an allowance to fix after the closing is key!

Key factor is - what is it actually worth to YOU and YOUR DEAL.If you can't get it for the price you require - then pass on it and find another. 

The key isn't to look for one of each, the key is to look for sources for each.

The key is to contact local banks and buy properties that cash flow.  

*Another KEY factor that a lot of people (including myself until I actually did a bunch of deals) overlook is rental supply/demand in a market.

The keys didn’t work to any units but one tenant let us walk through.

Or you can do cash for keys to get him out and find someone who can make payments on time and 3xs rent .

I would give him notice, and show up with your set of keys to let the work be complete.