They had friends in town and enjoyed entertaining.

It's possible the deal is ok, but your enjoyment percentage, even for 18 months, isn't that great in a unit like that.

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

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

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

@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. 

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

That leaves you with a good chunk of change to start the business and grow from that point with rental income/passive income coming in each month.If you have any specific questions and want to talk about Pinellas, Citrus or Hillsborough reach out I always enjoy talkng REI.

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.