I priced it only about 14% higher than the long term rental which matches traveling health professionals' budget on Furnished Finder.So I'm leaning toward longer term rental because even if I secure midterm tenant, that 14% more isn't really worth the potential vacancy. 

This helps you, as the buyer, understand the health of the asset.Where in the post does it say anything about what a seller makes?

Health and safety2.

You can always request Medical Documentation: Request documentation of her medical situation and a letter from her doctor to make sure her condition will improve and ask if she is up for taking care of the property while she is recovering.Check Her References: Contact previous landlords for references to get a sense of her reliability as a tenant.Lease Terms: You can always start with a 6 month or a 1-year lease option if you have a good idea of her overall health condition.  

Tenant risk is lease term remaining, sales/billings from the location, overall financial health of the tenant (i.e. solo practitioner with this one center as their sole source of income and declining billings, will not likely keep the property well maintained, and when they move out, you will have work to do), need for this use and/or competitive urgent cares in area, etc. 

My property manager is getting old and is having health issues.

If a lender isn’t responsive during the initial stages, I’ve learned that’s a strong indicator that it’ll be a painful process all the way to closing.

Cash-out refinance: this is a little painful with current interest rates3.

I think that they were just having a lot of growing pains last year, but they have ramped up and fine-tuned their customer service a ton. 

She's going to be a pain in your *** if you go under contract for her.