What is more lucrative in a Midwest or southern market, with  prices in the $300k’s for STR’s, college football or vacation spots and where.

I suspect this is true of most markets in WI, but not true of most vacation markets. 

After using the property as a for-rent vacation home for two years, the owner converts it to a principal residence.

We knew they were vacating so, we are really only 1 week vacancy. 

We NEVER, EVER, EVER, return a deposit until the tenant has vacated and we have inspected.

@Bryan Galaz the purpose of a HELOC is to use that money to invest, but you must be disciplined with putting the money back and not spending it on a vacation or expensive car. 

Currently, I am in Greece on vacation and my encode plus is off-line.

It sounds like you're embarking on an exciting journey in real estate investing.Investing in the Pocono area for short-term rentals (STRs) can be a lucrative venture due to its popularity as a vacation destination.Take the time to thoroughly research the Pocono area's vacation rental market.

While I would gladly accept an AirBnb booking, my property is less a vacation rental, and more a utility for traveling professionals/displaced families. 

Interested in purchasing a vacation home in downtown Seattle.