My line of questioning here is instead meant to make sure there's no "fear disguised as practicality" underneath the Schooling decision.Assuming the schooling is the right choice for you guys, does it have to be an all or none decision? 

I'd have fears about the tenant miss using my property, breaking the lease, or saying "I paid for 12 months so you can't evict me". 

This is what I feared I would hear. 

These questions will weed out some tire-kickers, and once the prospect sees the unit and expresses the desire to rent it, THEN I'd have them go through the application process.Also, try to schedule multiple showings at the same time:  it creates an 'auction' type atmosphere and will prompt a prospect to take action faster (fear of losing it to someone else).

Please tell me my fears are unfounded.

Either way, I hope it works out well for you all and that my fears are overblown.Good Luck!

@Roland Paicely I am a real estate agent and I still have fear of the phone.

Everything I've ever learned in my life was pretty much self taught, so I had no pre-existing skills when it came to remodeling or repairing a property.3) Fear.

I say that to say I am not fearful of Goliath. 

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.