It has been fixed in years, and the neighbors tree roots are wrapping around the pipes.

When that middle class family comes to a more affordable market, they're coming to plant roots.

The landlord tenant regulations and tenant friendly legislation is the root cause.

Next step would be to hire a structural engineer and get a detailed report of root cause and fix, however; I am thinking if its worth it for the following reasons...1.   

However, in a competitive market where deals are transacted much more quickly (and often times off-market), experienced agents/brokers with wide, deep-rooted networks, that facilitate transactions for a living will more often than not have their eyes on most properties before someone skimming the MLS will.

Putting down roots is vital. 

You need a more detailed grass roots analysis ... take all the things that will need to be replaced in time ... flooring, HVAC, plumbing, electric, roof, etc. ...

Something to keep in mind is that every tenant situation/problem posted on this forum has it's roots in a landlords inability to manage their business properly. 

Once she separates we are moving back to my roots in Clemson, SC.

For this first property I am thinking south metro just to put my roots down close to where I work/hang out.