The problem I may have is the condition of the property. 

Buy at a great price + location + good numbersRentals don't have to be rocket science.Figure rental rate based on like kind rented properties near by.Subtract: taxes, insurance, repair % (7.5%, but varies based on prop condition), vacancy (2 months), capex (5%, but varies based on prop condition/age), pm if using (8-10%).

Is he retiring to the good life on a beach?

We usually act as out own GC so I figured we'd have to do it on this job, too, but life would be so much easier if I could have someone handle it for $150/ sq ft. 

In my experience, if the property is in great condition, you won't' need the handyman more than two -three times a year top!

The Auction Asset Life Cycle: “Coming Soon”In this post I will discuss the asset lifecycle that properties on auction.com typically go through.

For me it makes sense to contribute to my 401k, realize the tax savings and simplify my life (by not managing additional assets in real estate).  

The apartment was always in pristine condition and they would actually leave and leave the apartment to us.

I've been reading BP on and off for over a year, I have been learning and involved in RE for half of my life 16+ years, never done wholesaling or mailing or anything 'silly', just what a 'normal' real real estate investor would do.

If you flip, then definitely refinish them.Floor life is a function of how many times they've been sanded.