I'm eager to learn from experienced investors and gain valuable insights into the world of STRs.

At that point in time, we can just list the property and sell it. we have long-term capital gains rather than short-term capital gains, we would have probably experienced some appreciation during that time.

So at the end of the day, M1 has become a huge part of my life and I have gained best friends and upped my investment, horizontal income, and career. 

As you get to this point your gaining more confidence in the options because you know option A and B had a certain outcome that wasn't option C, and this would give you more confidence you're doing the right thing for you.From there, I would be identifying properties to acquire if you don't already have some in mind and then my next sheet is creating the plan.

While there's no strict requirement to match the original mortgage terms, reinvesting the full proceeds without financing or using leverage to enhance returns is key.If you don't reinvest the full amount, any shortfall ("boot") will be subject to capital gains tax, and depreciation recapture may apply.This post does not create a CPA-Client relationship.

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 are neglecting to account for gentrification, which is the biggest REI gain or all.

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. 

If you lived there 3 of last 5 years consider the value of exemption on capital gains tax.

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.