Or, would my money be better spent someplace down south or by a National Park that would have year round traffic.My goal is to have a place where my family can spend a couple of weeks during the Summer, pad my retirement a bit, and have a place to leave my kids.Thank you in advance for your input.

You have $220k of gain - just leave everything as not aggregated, it will be a passive gain, and you can fully utilize your $200k of passive activity loss carryforwards. 

Thank you for leaving a post @Koren Lavi I appreciate the comment on not buying a house that works as a STR but not as a LTR. 

Water is rarely in the tenants name and that leaves Gas.  

If your tenant does not agree with the terms to continue on at the property he can leave.  

But it's missing a couple of integral features, such as maintenance requests/tracking, and also my bank (which I do not want to leave) for some reason has always hated connecting to Stessa and thus never works properly...

Personally, I don't leave anything consumable. 

I would charge it now so that it doesn't need to come off the deposit at the end leaving you with more deposit for any other damages.

They have no incentive to leave the place nice if they know they’re paying more than a personal maid would charge.  

@Jimmy Leaton depending on your situation you might want to leave the equity in the first house for now and just go buy another primary residence using a 5% down payment conventional loan.