Short-term pains for long-term gains. 

You get a deduction for the contribution, the gains grow tax-free and as long as you use the proceeds for health-related expenses the funds come out tax free as well. 

What are the terms/status on your current lessees?

Florida, particularly Tampa and Central Florida, is a strong option because of steady demand, landlord-friendly laws, and solid appreciation.If you’re debating between short-term and long-term rentals, I’d say long-term rentals are more stable, especially with the recent saturation of Airbnbs.

Last short term rental we put on the market was booked for a 30 day stay first day on the market.

I tend to shy away from homes over ~20 years old to buy and hold for long term renting.

Then do a thorough research on tenant applicants (note: leaving this to a PM may be hazardous to your financial health) and choose the one that is most “stable” with the best potential for long term tenancy.This advice is contrary to maximization of rental income, but IMO will reduce expenses of tenant turnover, property damage, property management fees so much that the difference in bottom line income will be quite small.  

I will no longer manage furnished long term rentals. 

Quote from @Peter Firehock: Introduction:Well you've certainly put together a long and comprehensive analysis.   

Quote from @Joy Daniels: As a short-term property manager I've seen how this industry changes so often—new guest trends, tech tools, and regulations seem to pop up all the time.