Most do-it-yourself services will help you obtain this as part of the package they offer, but if you just file the articles yourself, you'll need to go through the the additional step of applying with IRS to get your EIN.

Any mortgage that you apply as owner occupied  or then don't occupy will be considered mortgage fraud.

I've been doing some research and am stuck between deciding to apply for something along the lines of a property management company or real estate agency.

I've googled and have a basic understanding of what a revocable living trust is, but how does that apply to a real estate transaction?

Take the security deposit and apply it to the unpaid rent.3. 

Will we eventually establish roots to either permanently live someplace else or become snow birds?

If a tenant attempts to use the COVID moratorium, I believe they would need to claim that there was a hardship due to COVID - which I doubt applies in this instance.

@Christian WeberMaybe if you buy using a conventional loan the 100 miles rule doesn’t apply

You send them an invite to apply and they pay the fee.

I was looking into the Residential Landlord and Tenant ordinance but it was unclear to me if my situation applies to it since it states "The ordinance covers most rental properties located in Chicago except units in owner-occupied buildings with six units or less; most units in hotels, motels and rooming houses, dormitories, shelters, employees' quarters, and non-residential rental properties, and owner-occupied co-ops".