Were you just looking to gain your time back?

We can use the original part of the house for rental as well, which is valuable to help use understand the STR rental market better, ie what income we actually get as all we have current is the airbnb site itself and airdna (an airbnb analytics site).In short I think the downside is limited, and this deal with give valuable experience while testing my beliefs that it will make me some money!

Without a doubt, having more experience in the field is valuable.

Quote from @Jay Fayz: Hello everyone,I've recently been exploring real estate as a potential career path and I'm looking for advice on the best entry-level job to gain experience and knowledge.

If I can park the 388k ($415-27k) for one year at CD rate of 4.5% and then est 300k (after paying cap gain/depr recap) at 3.0% (assume CD rates lower) that interest income of about 24 months net of ordinary income tax is about the same as my current mortgage.Trying to play devil's advocate and think why selling this year does not make sense. 

That number seems high but the neighborhood was “hot” and houses sold really quickly.What I cared about most was completing my second deal to gain experience.

You get a deduction for the contribution, the gains grow tax-free and as long as you use the proceeds for health-related expenses the funds come out tax free as well. 

Managing your own property and finding tenants is a great way to gain hands-on experience.

If the property fronts on a state road, you will need an Highway Occupancy Permit from Pennsylvania department of Transportation, to gain accces to the road. 

I'm looking to gain momentum and scale fairly quickly.I'm going to try rentredi and quicken to manage the numbers.