Develop a clear set of criteria for onboarding clients and stick to it.

We found that we were often outbid by novice investors or that the bank set a reserve price so high we couldn't make the numbers work.

Research local market rates to set competitive rents, and consider offering utilities or furnishings to attract tenants.

Teach an introduction to real estate class with in a high school setting!

Switching property managers seems like it was a smart move, especially with how much you and your wife had to step in before.Chicago definitely isn’t an easy market, but it sounds like you’re set up for better success moving forward.

As your base level of knowledge grows, you will start to develop a clearer picture on the things you want to do, and where you skill sets lie, which can narrow down who you may want for partner.  

(B) Setting a "code of conduct" for the "if".

I would start by setting expectations that you will likely not be able to net as much as you would if the property were vacant and turnkey. 

@Justin BradburyTo kick off your path in real estate investing, you need education, networking, setting goals, analyzing deals, and starting small.

Your cabin will be set apart by the above, not by things you can get at Lowe's or Walmart.