In this situation we have a former-tenant  hyper sensitive to return of full security deposit (when unit wasn’t returned in good condition) and we are  experiencing a few unique damages.

They found that targeting traveling nurses and medical residents provided reliable income, especially with amenities like a washer/dryer and blackout curtains.. details that are often overlooked but highly valued.For STR potential, I’d suggest researching local tourism data.

If there's a hole, it may be a red flag.b) sensitivity analysis: I examine all the assumptions, and make sure I can live with the worst case scenarios.c) "Stall and see": if they are getting money over multiple years, and there is no penalty for investing later, I would usually wait so I get some real performance data, versus having to look at theoretical pro forma information.d) Recession stress test: I will not invest in anything, until I subject it to recession level stress and see if I can live with the result.

For example, areas like Chicago have a strong demand for furnsihed rentals, especially in neighborhoods near medical centers.

part of a current medical campus? 

$300K is a lot of credit card debt and probably didn't happen overnight (unless it is medical bills). 

Things that have stood out so far in my research: 1-Close proximity to Metro North (90 minute ride to NYC)2-Vassar Medical Center3-Marist & Vassar Colleges 4- The Walkway over the Hudson5-Restaurants/Cafes/Hotels, etc.Thanks for your time.

An time sensitive opportunity came across my table for a purchase of properties in a bundle.

You cannot just casually start this medical expense plan, it's not an IRA.

There is still a trickle of traveling medical professionals, but I see a lot of relocation needs.