Seeking advice on how to optimize real estate portfolio

[Julie Kent]

Hey all, 

I'm a newbie to Bigger Pockets and would love to get the community's advice.  I fell into real estate investing accidentally - I have two rental properties that I originally purchased to live in myself, and then when I wanted to move I couldn't sell so I turned them into rentals.  Here's a fairly concise overview of my properties: 

68th St: 3 bed/1.5 bath; Current Zestimate is $154K (purchased for $122K); mortgage balance is $70K; net $367/month cash flow; 12-month lease tenant will expire 4/1/2018

Tanglewood Dr: 5 bed/3.5 bath; Current Zestimate is $411K (purchased for $292K); mortgage balance is $220K; net $540/month cash flow; 6-month lease tenant will expire 11/30/2016

53rd St: 2 bed/1 bath; Current Zestimate: $86K (purchased for $75K); mortgage balance is $54K; net $406; 12 month lease tenant will expire 1/1/2018

Total net is ~$1,300/month 

The 53rd St house I purchased about a year and a half ago.  I've sunk a ton of money into it; my first tenant had to be evicted and trashed the place.  It's needed a wall anchor, a paved driveway (I didn't do my homework on the city rental permit regulations... they require a paved driveway) and new windows.  Bottom line is that if I sold it'd be at a large loss.  

My question is what to do with the 68th St and Tanglewood properties as there is a decent amount of equity in each.  I feel like I have a lot of money tied up that could be put to work if I sold.  I've considered selling the Tanglewood property and utilizing the proceeds to pay off the other two mortgages, or I could sell the Tanglewood and try to buy 2 smaller properties similar to 53rd St that would bring in ~$400/each.  Or possibly a multi-family.  

I'd be curious to hear anyone's thoughts on the best way to manage my portfolio moving forward. 

Thanks,

Julie