One smaller note, Cook County just reassessed taxes and it's a pretty big bump (at least on my properties before I go to appeal). 

I've pretty much limited myself to duplexes for that reason.

This is my first deal so i've been pretty conservative by plugging in worst case scenario numbers, to the point where monthly cash flow is close to 0...

I wouldn't put too much weight on what grade it has per the county website, as that is pretty general. 

Plus tenants might move at an accelerated pace because of the increases and this could throw your occupancy pretty low and even into negative cash flow. 

My passions and hobbies are woodworking, motorcycles(still saving to buy one) skiing, and pretty much anything outdoors.

I found a "highest and best due by tomorrow" home I'm really excited about listed for about $100K less than the going rate for the neighborhood, accepting only cash offers, presumably because of the sagging roof, foundation issues, fact that it was built in the 1900s and pretty much never updated, etc.

They buying costs pretty much made the deal not so attractive.  

That's pretty spot on what the market is currently charging. 

I have done a bunch of reading and watching videos on it and feel like I'm pretty knowledgeable on it.