And finally, while Class A properties tend to have low capex/deferred maintenance due to age, relative to Class C and D, if there are capex items that are not accounted for it can cause any class property to run into trouble sooner than properties without deferred maintenance.

I'll probably save him a minimum of $5000 on his loan, but chances are another $10,000-$15,000.If the house you want to buy has a lot of repairs needed or deferred maintenance, there is likely a lot of stuff you can't see or isn't disclosed.  

If so, why not defer to what he has to say about it? 

@Ben Cochran, The entirety of your sale has to go into the purchase of the land and building if you want to defer all tax. 

It sounds like you could sell it rather easily and then 1031 (tax deferred) the funds into another project, maybe a quad that is in the right area to short term, etc.

Well, people who are flush with cash or equity from the last 2+ years of crazy appreciation in real estate and the stock market. 4) Some investors are OK with buying low to negative cashflow for the first 12-18 months while they stabilize the property, increase rents, and fix deferred maintenance items.

But to defer all tax you must do two things:  First you must purchase at least as much as your net sale (contract price minus closing costs - $220K ish). 

I think we are all speculating based on the fact that you say there is a lot of deferred maintenance and updates and the tenant is okay with it at the current rent level, that the current rent level is very affordable and a $600 jump would be massive.   

It is not that simple and it may be more accurate to say deferring taxes.

Unless we are talking about a very large capital gain deferment, it's usually better to keep it simple.