I would look up builder supply houses and see if you can get windows to fit. 

Then you just find areas that fit that bill. 

It needs to be a sublease agreement, and unfortunately there is no one size fits all option from the Chicago Association of Realtors.  

I would suggest joining MeetUp groups via Zoom and you will get the opportunity to network and see if the area is a good fit for your investing requirements/potential.I hope this suggestion helps and I wish you all the abundance and blessings in your real estate investing activity.

Judging the appearance of the typical Salespersons that I have seen in my time working for the top 10 Financial firms as an IT Specialist, I just don't fit in physically.

It can be a can of worms to start demoing that and if it fits with the rest of the house it does actually look good.

They make them small enough to fit handrail hardware and long enough to get into the masonry.

they are hustling to show their worth for their origination points which I think is not worth it unless you have some rare situation or don't have the time yourself to find a lender / loan product to fit your needs. 

I am looking to Flip in general or BRRRR, if the opportunity is a better fit.

Less work in the immediate future because you don't have to retro fit.