If you find it to be a pain to manage yourself hire a management company to do it for you. 

That is painful because this is small town in Midwest and 2 bedroom rent is $550 a month.

It will be a pain in the butt to turn the property over so quickly.3.

Lots of people move to the fringe because they can't afford anywhere else. then when the market softens, those areas get hit, and painfully so.However, another strategy is to make sure you're looking at different product type as well. hedge funds beat up a specific category in Sacramento and the Inland Empire driving the prices up quickly to where they don't make that much sense.

Hire enough losers, throw enough money away until the memory of the excruciating painfulness of the results of saying yes to someone you should have said no to is deep enough.

The main reason I'm tempted to sell now as I could really use the capital for other investments and managing a co-op in NYC is a pain...Glad I asked for advice on here as I'm thinking it would be unwise to sell at this time.  

My late fee is PAINFUL by design, $100 USD. 

That one is been a painful learning curve for me.

The reason I ask this is to help all of us better understand your goals and thought process.I have tons of suggestions (as I'm sure others do), but without your goals / desired outcomes, preferences, comfort level, and pain threshold, we're just taking shots in the dark.

OMG;  Truth is painful, ain't it!