Quote from @Andrew Steffens: Pricing and multi channel approach is very important nowadays In today's market, I think you hit the nail on the head.  

I still consider myself fairly new to this world, and I can say with 100% certainly the biggest battles are the internal ones, and this industry has given the pleasure of being forced to address several of my short comings, and continue to address them all the time.I find I get the most emotional when I get reactionary, so my constant focus is around honing and suppressing reaction as a whole both internal and external.Thanks for taking the time to write this up.This part is right on the nails - "I find I get the most emotional when I get reactionary."

I have done this in the past for guys that got nailed in the states they were working in  Mississipi for one. 

It allowed me to preserve my personal savings while still securing the capital I needed to get the project going.

@Katie Casper Colin hit the nail on the head: North Conway has more STRs than any area of the state.

If you ever want to see the difference in person, just try running a cheapo Chinese nail into an old-growth 2x4 and watch it bend in half. 

Or put another way, they will find a way to nail you.

Get that management company nailed down now, as they should have better marketing strategies so you can take those off your hands, and it allows you and the management company to align and manage expectations from day one. 

Buy and HODLing will always reign the best course of action; sell preservation mechanism physical assets on rallies due to turbulence, and buy back in times of peace and ease.

You're on the right thought process to preserve you $ and build wealth, a duplex is a good start but I may have a better real estate suggestion that could build wealth faster while doing a house hack.