He’s clearly trying to play a tough guy, but it’s irritating that he decided to play it this way.

I'd just make sure you have a VERY CLEAR SCOPE OF WORK no matter who you work with.If you decide to use someone besides your property manager, you need to have BOOTS ON THE GROUND that can view the property a couple of times a week at least! 

We have about $200K equity in our home, both of us are independent contractors / business owners who write off a lot on our tax returns - so I’m not clear if we have to take what we can get or if these terms seem in the realm of normal.  

Meaning that the property must be free and clear.

To be clear, I will keep working but want to be self employeed in the home services business.Looking forward to see what I can learn from this community.Thank you.

The clear and obvious answer would be to instantly pay the back taxes and offer a small lump sum for them to move with and just lowball in whatever structure works for the both of you weather that is a better sale price or a greater monthly payment to them and just find your middle ground that works out for you both.

Hey @Michelle Martin - I am the same thought as @John Warren, if you have a decent Chicago Eviction attorney they should have a pretty clear understanding of the process and be able to guide you through the next steps.  

As a hypothetical, let's say there's a syndication seeking capital....Total capitalization $30M, Equity raise $10M....clearly this falls within the boundaries of where a family office, private equity etc. check writer would become involved if the deal has merit.

Can the lender still file the lien after-the-fact as long as the promissory note clearly indicated that the intent was for the subject property to be collateral?

There 50 other leases in the building which clearly specify a 1 yr term then go month to month which Im sure was the intent here but the leasing manager neglected to fill out the info.One of the weirdest lease things Ive seen.