Hey @Mordechai Chaimovitz - It sounds like you are talking about Chicago's NW side because there are definitely tons of areas in Chicago where a 2 flat can cashflow well.I know for me buying on the nw side was critical to my personal well-being and life happiness. 

Real estate success is driven by demand, it sounds like you will have more tenant options and higher prices in Ft.

This is the reason I quit being a moderator because of something that went mildly off the rails in the forums, and then it was completely censored because I responded to staff in the forums after they mentioned me.I think the moderators do an amazing job and should be given more pay or credit or anything.

The property will need to have a slight rehab to get it up to STR standards, but when complete it should easily be a $200k Gross booking revenue property.

what you're proposing, while possible, is incredibly difficult and highly risky, and i don't know how you would do it completely remotely with no plans to visit or set up a team.i think i've said this in other posts, but there is tremendous demand for inventory right now among both retail buyers and investors. 

We go above and beyond when it comes to protection.. starting with insurance coverage, sings in the listing and in the property that there is no guard on duty (as silly as that sounds), putting extra locking device high enough so youngsters can't reach, an alarm/beep system to alert them that door opens for those with small children (or elderly) so they cannot wander out in the backyard with no one noticing and risk drowning.

Getting the application and fee for the first lease completed now.

New tenant must go through complete vetting, sign the lease, pay security deposit and rent, and move in, prior to the referring tenant getting their $100.

Yeah, I completely understand.

Most are going to want to lend on the rehab as it ensures the rehab to be completed,There are numerous ways to pencil it out in your favor though.It benefits to work with an experienced broker who can guide you through the process and put you into the best possible product and solution out there for you.