We have an exceptionally strong health care market that is stabilizing employment.

Not drinking the Kool aid maybe?

I would be much happier working my current job 1-3 days a week (earning ~$40/hour), which is realistic as I work in healthcare and per diem work is common, and supplementing that with income from other sources including real estate investments. 

@Christopher Hunter Yes, I've taken a look at Marcus & Millichap, as well as a couple of other sites for some research on it, figured would help to aid it with locals and deals that are down there to start analyzing personally.

Some will say rip of the band aid and raise the rents (assuming you can do so legally). 

You may need the aid of a property manager to do this right .

Pittsburgh PA is a city on the rise due in part to the technology boom in our area, a strong established healthcare system, A Mayor and our County Executive who are very proactive on initiatives that are attracting big businesses, a strong recovering economy and the continuation of new construction.

It would seem to me that health care is more recession proof than other types of businesses, doctors would be [relatively] easy tenants to have, and the price point of these condos are not price-prohibitive. 

Portland is a large city, and I"m sure there's housing advocates there, or legal aid.

You're not their financial coach and I also don't feel that a landlord/manager's job is to ensure that the tenant has explored a variety of aid avenues.