Get it under contract and then scour the earth to find out what is wrong with it.

Google Earth down to all the commercial shopping 1-6 block radius, look for boarded up windows, broken windows, Grafitti, types of cars, types of people, trash etc... if you see all of the above.

Why on earth would you wait until she was shorting you rent to take action?

If he sacrifices now, he could have cash-flow for years to come.  2 jobs and a scorched earth budget for 12-18 months in exchange for a potential cash-out refi in 24 months and long-time success. 

Series XX, CFA, CIPM ect. 2) This most likely won't be terribly earth shifting in terms of RE syndication since the subset of folks who work in finance and already aren't accredited is pretty small.This entire post is the result of no more than 15 minutes on google and to much coffee, so give it as much credence as you normally do things you read from random people you've never met on the internet.

You mention that he's hard to get in touch with.This might become very important halfway or more typically 3/4 of the way into the job, when the handyman decides it's time to drop off the earth for three months.You can also expect that the handyman will want to be paid proportionately or ahead of time as he completes work.

Down to earth, responsive, very affordable, seems excited to find ways to save you money.

It also has loose/damaged siding, security bars on windows that need to be removed, earth-to-wood contact in the foundation and siding, leaks in sinks, windows that don't stay open, loose toilets.

Because I'm remote I've already done a large 'tour' of the area in Google Earth and it looks like a good area.  

I like the Wack a Mole analogy.. if I think back on my career in this game that started in 75.there were all distinct and different events that perpetuated a slow down or price compression in real estate75.... coming out of VN war  soft economy83 - 85  sky high mortgage and interest rates  ( SL crisis  but a lot of money was made picking up those deals)89 to 92  in bay area  Earth quake and war.. prices in SF and bay area compressed 20 to 50%  ( we have short memories.) but that was also pre high tech.2000  dot com bomb  short lived 2001  Bin laden short lived07 to 2011  global credit crisis worse i have ever seen or I think any one basically living ever saw.. worse than great depression in many areas...