@David Simon I haven't tried using those sites for comps but I use Zillow and put "Recently sold" then play with the filters to get something close to the house I'm looking for.

@James Nghiem I would recommend Whitney with Above & Below 1031 as your QI.

About your comment below "Hanging onto a poorly-performing property just because it will be paid off some day doesn't really make sense.

There are many BP members who must have awful 401k plans with no match for all the hatred we hear towards them.If you are not going to be working and your taxable income will be low for a period, you may want to consider a Roth conversion ladder to allow for tax free distributions of 401k account balance.

The prevents people who forget to shut their tstats off in the summer from using heat when a night dips below 70.

Overall, I think it is a solid deal, especially if you can keep expenses below the 50% threshold.  

Below is the spreadsheet analysis. 

If he did a full rehab on the units and others in the same complex go for $593k is he really that good a friend to sell something almost $300k below market value?

The options might be a cash or traditional financing offer 15-20% below market value or full asking price, but your terms (which may include seller financing with discounted or delayed initial payments, etc.).  

Vacancies, except for a period in 2015 - 2016 (management issues) has been below 5%.