NOD is public record.. one can subscribe to Property Radar and get all this info for a very low monthly fee plus a ton of other add on' like CRM and auto mailers etc..

Is there any flat fee lawyer in Chicago that can help me file this?

Existing security deposits are unaffected here, but we are no longer allowed to collect more than one month's rent in deposits and fees. 

But the damage was done—I had already gone through three management companies, three evictions, and a lot of lost rent and legal fees.

Buy a townhouse in this development near where I live called Sea Colony:Details: $860k for a comfortable townhouse.Pros:Comfortable place to live for the next few years, and I’d still have liquidity to invest elsewhere.It is still in my current community where all of my friends live, so I would still be where I want to be location-wise.Will get appreciation.Cons:High HOA fees ($660/month) and potential 10k special assessment in the next few years.Likely won’t cash flow after we move, so unsure whether it would make sense to hold.3. 

I previously used free services like Cozy (before merging with Apartments.com) and Rentler ( before merging with another company and charging fees for ACH payments) but now I use them as an all-in-one PM solution for the most part.

This means that you will probably need to pay registration and filing fees in at least 2 states if you don’t buy CA property as a CA resident.Any lawsuits should be limited to the assets of the LLC and not your personal assets (assuming you run the LLC appropriately and the corporate veil is not pierced, some debate as to SMLLC).

We’re wondering if these fees and processes are standard for short-term rentals.

Those loans do come with some restrictions and fees for the life of the loan. 

A lender with a real estate license can NOT pay you a referral fee for sending him a loan.