I've seen it happen.A home run scenario would be to acquire or build several buildings that would cover the continuum of elderly care. 

I would need to use it as a STR part of the time to help cover the costs and for tax purposes, but I'm not really looking forward to "operating a STR business" and don't need a lot of extra cash flow (I have W2 job that I truly enjoy). 

We financed the Dearborn St project using our standard Partner Driven strategy—covering all the necessary capital for the acquisition and renovation.

These are typically more expensive but can be more profitable.Condominiums and Townhouses: These can be lower maintenance compared to single-family homes and multi-family properties, as HOA fees often cover exterior maintenance.

It seems to break even on my calculator at that point, but seems risky to have to cover the refinanced mortgage. 

That would not even cover the expenses.

We've had only 5 vacant nights from then to present (May 2022) and our income ranges between $2500-3000+ a month which more than covers our mortgage.

If that's what you're getting at, that there might be drama between them that effects the property writ-large, then those should cover it depending on the verbiage of them.

NYC is the obvious central point but the restrictions seem to be covering northern NJ and most of Westchester now.

We use STR through airbnb and cover most of our mortgage.