I was either channeling my inner @Steve Vaughan and taking a nap or driving through Kansas and MO with triple digits on the car thermometer -- the nap sounds better.

My goal is to buy what flippers say "does not have enough meat on the bone", a B- condition on the surface property but with good internals, in an A neighboorhood, then fix it up over time so that it's better than average. 

Adding value to the mentors life is your goal!

This is a very valuable approach and time saving as well.My goals are fairly ambitious, as they should be, to retire from "employee" status within the next 5 years.

My goals are to start with some fix and flip rehabs, possibly wholesales and leverage my way into multifamily and eventually commercial buy & hold properties.

Read business books, REI books, economics, investing, personal growth/goals/motivation topics.Start tracking your net worth with an app, personal finance software or a spreadsheet. 

Assuming the market rate for these units is $700, and the area's vacancy rate is low, having a goal to get all units to or very near market rates is the way to go.  

My goal is to be all in at 70% - 75% of ARV.

Long term goal is single family buy & hold, and ultimately small multi-family buy & hold all in the NW suburbs (Woodstock, Crystal Lake, Algonquin, Huntley, etc), and to replace my FT income in the next 2 years.

Given the price/rent ratio, I agree w the above that this is not a good place for REI, you'd likely want to sell to families who wanted to live in a good house in a nice area.One other suggestion for how you pitch this place: Billing it as "Near Rice" may do more to hurt than help your goal of selling it.