Go to Etsy and search for "rental property tracker," and you will find hundreds of nice spreadsheets to track 10-20 rentals, usually for under $10.Software has extremely helpful features like online payments, marketing syndication (click a button, and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

Why will likely determine how because if you are looking for cashflow vs. appreciation vs. quick capitalHow could it be househacking, brrrr, flip, long term -> You mentioned BRRRR, which is an awesome strategy but will only work in specific sectors of Chicagoland. finding the perfect brrrr in the current environment is extremely tough!

I also would not overlook the power of joining Facebook groups for people looking for rentals, especially if you are placing a tenant yourself.

However, 190 days seems extreme.

We both have made compromises along the way.I think that’s completely right and one of the reasons you hear the horror stories about these things going sideways (there’s no established timeline for exit), it literally just goes until something breaks. figuring out the ownership structure, and thus the use/access, as well as the exit feels like the two biggest items to get extreme clarity around. 

The power of tax-free compounding growth can be really meaningful over long periods of time.

Part of being a landlord gives you the power to help people who need a break so it's in your hands to look at the record and say, that was a long time ago, now he has a good business.

I've known relatively new and extremely fancy houses in Madison County that developed the same foundation problems.

It is also extremely high.

Thank you for your time. not having hte capital and no other assets to secure the property for a fix and flip is going to extremely challenging.