I've begun digging into research and am seriously considering shifting my strategy back to buy and hold, as I fear the window for flipping may be over.I'm interested in knowing how other investors are thinking about approaching the Chicago market as we end 2017 and prepare for 2018. 

It is about what everyone here can achieve if you put your head down and shift into 5th gear without looking up until you shatter your goals.

Also, does anyone have any good tech tips on systematizing, streamlining and organizing driving for dollars info?

I think my strategy will shift as I go, but right now I want to maximize the monthly and free up cash to reinvest.

Don't go too fast, after a few your strategy shifts and becomes more focused.10.

Purchased in 2015, did a streamline refi in early 2017. 

I'll gladly exchange a few hours of physical labor to pick the brain of an investor with 25 years of experience (Lesson 2: Come from a place of service when looking to work with a mentor).After a day of driving, loading/unloading the truck, we were approaching home, when my investor friend mentioned that he was looking to shift a property out of a portfolio. 

If Mark did the work and paid for it, that would be an expense that would lower his NOI, if he lowered his rent instead to the same costs that it would be for him to finance the work, his NOI works out exactly the same, he would just be shifting the cost yet he would have less risk and gain on the value from the remodel work. am i thinking wrong on that ?

This is not my area of practice, but I hear from colleagues there are some streamlined options for getting through probate if there is no dispute between possible heirs.   

Bottom line, you are shifting debt from  one loan that is fixed and low interest, to another that is variable and higher interest.