Plus i have had some health issues which has caused me to work a lot less.

This might offer more security but also could complicate tax reporting.Taxation of Y as an S Corp:If Y is profitable, electing S Corp status could reduce self-employment taxes, but it also comes with more stringent IRS rules.

I would "run the numbers" - two scenarios - status quo vs. refinanced + new property

Individual markets vary for sure but overall health of tourism industry is definitely down.

Consider paying down the high-interest debt strategically if it outweighs the potential returns from new investments.Additionally, understanding Real Estate Professional Status (REPS) and Short-Term Rental (STR) tax savings can significantly reduce your tax bill while building your portfolio, enhancing your overall financial strategy.

We have programs that we readily pay your; grocery bill, rent, cell phone, internet, spending money, health insurance, Rx coverage, day care AND to boot not only do you NOT have to pay diddly-squat in income tax's that the rest of us subsidize (pay) for you but we even send you a big fat check each year if you have kids. 

I also came across the following article which reviews why LLC as a structure is not the way to go.http://www.moodysgartner.com/canadians-beware-united-states-limited-liability-companies-may-be-hazardous-to-your-tax-health/I also found the following to be informative.

A large home for seniors who need minimal/no health supports with shared kitchens and bathrooms.

Each choice has its own set of risks and benefits, so it's critical to consider your financial status, investing goals, and Cleveland market opportunities before deciding on the best strategy.Good luck!

Be careful how you word any of this though, if you had told the tenants the adult son could apply but not his wife and daughter it could be familial status violation for fair housing.