Verifying last 2 years of rental history and income extremely important to find the “best of the worst”.Make sure you understand the Class of properties you are looking at and the corresponding results to expect.

Consider all revenue and expenses and calculate best and worst case scenario.

Are there strategies or options you can recommend to someone like me, who is both just starting out and has limited funds (worst combo ever?)?   

That's sort of funny, sort of a red flag for me. 

It's the worst place in the world. 

And just rode the wave of RE through all sorts of different RE ventures..

What’s the worst-case scenario for rental prices during winter?

I agree that the sphere of influence created by going through the degree process and meeting all sorts of folks related to it could be huge for opening doors that may or may not be missed without it.

The larger strategy for the big income change has sort of been set to the side while I've been in transition.

Another unfortunate situation with a lot of these sorts of tenants is that they are "judgment proof", meaning, even if you were to sue them for damages, they do not make sufficient income or have sufficient assets to collect on your judgment.