We stayed for three years, and then bought another two flat in Lincoln Square, repeating the same process while making the Bucktown property a full-rental.

. - i.e. digital door locks, wifi controlled thermostats, ring camera on the exterior entrance.  

Right now all three of us still have W-2 jobs on top everything else

With these three data points, you can arrive at the expected value of the property. 

From what I've read (no experience), it boils down to three things:1.

We've put three in this same range under contract in the last two weeks.

Got a parking pad that can fit three cars but only need 2 for the tenants.

I'm working 70 hours a week and while I make great money, I have no time for my wife and three children. 

We have a contract on three more plus 1 we are making offer on this week. 

:@Joe VilleneuveTelling someone to sell what they just bought and start all over is probably not cost-effective for them.Right now he has a major safety net and in a great position to start leveraging, if he wants to, or continue to cover his butt with more owned assets and cash flow before he starts leveraging.The answer to my three questions says otherwise.