Should We Sell or Not?

[John Berger]

First timer here: My wife and I bought a house in 2015 for a great deal $123k for 2k sq ft. We finished an upstairs bonus room to make it 2600 sq ft. We now owe 105k on the house, but we aren't set on staying there long term (don't like the back yard, long commute, less than ideal school zone). I've done the math and after we sell, we could make $50-55k after closing costs/fees which would take care of my wife's student loans and help with a down payment on a nicer house that we could see ourselves in long term. 

We did the same thing with our previous house too. Buy it, fix it up, resell it, but for some reason we seem to have more reservation about moving this time. Looking for some more objective thoughts on this. Thanks forum!