What is your peak season? 

Check to see if this is a legal duplex!

It's a 2-unit house, if that matters at all. 

Any general advice is much appreciated.You should house hack to start.

Somewhere in the middle is likely your best bet for a 20 year timeline.I have almost 50 units here myself and that's about what my portfolio is cash flowing at this point combined LTV is around 65% as loans have gotten paid down and values have went up.

Let’s be real: Not every deal is going to close. 

But if I sold today I likely would lose atleast 10k.Would it be feasible to just relocate for the job and rent the house for the time being and see what happens?

From out of the country with a house that you did not see??

Leverage your construction skills for flips, start with smaller projects to minimize risk, and consider house hacking or long-term rentals for a steady income.

I think a lot of the midwest cities will capitalize on that in the coming years with the housing affordability issues the country as a whole has been having.