Sit down with them, express your interest, and ask how you could partner together to learn the ropes and dip your toes in the water.

While you are here and learn about the market perhaps buy a rental that you could analyze as an investment. 

Right now, I'm in the "knowledge gathering phase" and actively putting what I learn into action.I have a fantastic team of investors, a legit buyers list, and resources for finding deals.

Take your time, learn and try not to get too attached to the house.

From what I have learned from both the internet and colleagues is that the finances are the hardest part of getting started.

The duplex will still work quite well if I need to pivot back to LTR and even mid term, but as stated before, the property is quite profitable when it was able to be done as STR.I see these challenges as new opportunities to grow and continue to learn and improve my craft.Thank you all,James

Con I would say is that you have to do the work or pay someone lol Its a great way to learn about how to rehab properties without having to stress about any timelines. 

TBD Lessons learned?

TBD Lessons learned?

Chicago is MIXED BAG of general contractors and architects PLEASE be sure not to rush or use the cheap guys...one of my favorite sayings (that I have learned the hard way):"BEING CHEAP IS EXPENSIVE"