I'd bet you'll be able to find some really good deals across the bridge over in Superior WI.

This definitely gives me more confidence to pursue the safer option right now--at least to start out and get my feet wet first before taking something bigger with more risks. 

But I bet you could find the right deal if you’re patient.

Your best bet would be to understand your local market (or the market where you want to invest) by going through the T12 of the listed properties.

If its your parents money they might need the safer path of keeping it and raising rents on it if possible.

Save up an emergency fund (3-6 months of liquid cash, how much will vary based on who you ask/read), then put everything that is left into an account to save for a downpayment, closing costs (although asking the seller for closing cost assist is also a great plan), and some reserves for whatever "little" issues come up with the house.Then come back to it in a year and you will be in a much "safer" position.Best of luck.

You getting a Deed In Lieu is probably your best bet.  

Higher cash flow areas or "safer" spots with better school districts and the like?

Easier and safer for you to get a note and mortgage/Deed of Trust IMO.

Best bet would be to contact all the big ones - CBRE, JLL, HFF, M&M, SVN.