Any advice on what setup is easiest and most tax advantaged?

From there it's running a schedule and taking responsibility for my actions.

Rent payments from the medical LLC are fully deductible as a business expense, while the property-owning LLC will report the rent as taxable income, which can be offset by deductions for expenses like mortgage interest, property taxes, maintenance, and depreciation.To ensure compliance, document how FMV was determined—using market comparisons, an appraisal, or similar data—and draft a formal lease agreement outlining the terms, rent amount, and responsibilities.

Yes, do the tax exchange if you can.  

Consult your local CPA to calculate accurately and minimize your tax liability.

@David Hyman we recently started this group - will be scheduling the next meetup in the coming dayshttps://www.meetup.com/long-is...

You would have had to be there for at least that to save on the capital gains taxes (up to 250k). 

He scheduled maintenance and did quality control on cleans. 

Can you either rent out your current property if there’s been little/no appreciation, or sell it tax free?

Sell, get the tax savings while you can.