But let’s go a later deeper - my down payment would come out of a well performing stock portfolio.

Happy to help if you need more guidance, my partner and I have a portfolio of STR's in the area.

Hi Michael,It’s great to hear about your interest in growing your commercial property portfolio in the Chicago area.

@Joe Frank I’m a huge fan of Turbo Tenant to market properties, manage leads, screen tenants and lease up.

You should consult with local property managers and find what the average DOM would be to lease your home and rental rates etc. this would be a good starting point. 

From what I've heard, local banks are sometimes more flexible than the big guys.A buddy of mine managed to snag a HELOC on his rental property, which isn't always straightforward, but it opened doors for him.

I also recommend you start looking for a professional property manager, at least until you educate yourself enough to run this solo.

She is moving out and next management company sent me a questionnaire and one asked "Did they have any animals on your property?

Your goal is to build a passive real estate portfolio (we can discuss what passive means to you), so while I don't condone throwing $100k into a deal without even a basic understanding, alternatively doing so will teach you far more lessons than reading a book will.  

It sounds like you've been through a challenging process, but it's great that you're continuing to build your portfolio!