Strategic or Shortsighted? Would You Sell If You Were Me?

[Cosmo Iannopollo]

My wife and I have recently begun looking into flipping properties, to the point that I have liquidated two retirement accounts to fund this endeavor. One of my biggest assets towards this end is a two-unit multi that I purchased in late 2014. Here are the particulars:

Purchase Price: 200K
Mortgage Owed: 182K
Probable Sale Price: 230K
Monthly Mortgage Payment: 1,600
Combined Rental Income/Mo: 2,400

Considerations: 

The house will need a new roof within the next two years 
I am living in a different state as the property
The rental market is solid, with Yale, Yale hospitals and a Coast Guard base nearby
I lived in the house from Dec. 2014 - Sept. 2017, allowing us to take a tax-free profit
I do not have enough equity in the house for a HELOC, and probably won't for another year

Am I being shortsighted here? Any sale proceeds would go a long way towards adding a cushion towards our flipping endeavor and/or allowing us to take on a bigger project. 

Also, 1031 is probably out of the question as I may want to use the funds to eventually buy a primary residence for the family. 

[Cosmo Iannopollo]

@Brandon Yeager Thanks for weighing in. Made the decision to list it. My biggest fear is being short sighted but at the same time, a property manager for one property doesn't make sense, and landlording from a distance has always made me uneasy. 

Plus, that extra 25-30K could be a huge boon for us.