Hopefully the high season does well.  

Be a Financial Partner with a seasoned investor that knows the market and be involved to get to know the how to's.Reach out to me if you want to talk more. 

Great thing about Bigger Pockets is you can network and find in any state a great property, seasoned agent, Banker for financing, Wholesaler, GC, handyman/property maintenance to make it all happen.

It depends on the market, size of pool, type of pool (liner, gunite, fiberglass), insurance at your location, availability of qualified pool techs in your market, indoor or outdoor (seasonality or year round), heated or non-heated to just name a few. 

Odds are there is much more hidden here than is being shared.A seasoned investor could probably mitigate these risks, but they would run EVERYTHING to ground. 

To my seasoned investors, what makes the most sense in the area/market?

We also plan on short term renting our house for peak season in July and the start of August next summer.

Will it put you into the slow start of school season? 

You need to find a good Property Management company to keep you're place rented for seasonal rentals or long term rentals.  

I am a seasoned multi-family property manager and have experience with many platforms.