@Daniel Stoychev for me personally I’m open to investing most anywhere if the deal is right by the choice between Cook County or not Cook county I will always go with not Cook County. 

More specific: how do you personally keep records? 

I personally don't like condos for a rental property.HOA feesHOA rules that can change.

Correct, which means that "not on your personal record" is not actually factual.

If someone injures themselves and sues, they will be suing the LLC and not you personally.

Has anyone filed taxes yet as a W-2 employee who owns only STR, rents for on average less than 7 days per rental (STR), and materially participates (usually requires 100 hours or more in a year and more than anyone else)I’ve heard there are amazing tax benefits if you fall under all of the categories.

You would just need to file an amended return for the year you bought the property to claim the depreciation you didn't originally take. 

However, if you're setting up the LLC to file as a business with a separate tax return there might be some advantages to a loan.

All four units are occupied and the tenants are currently paying their rent via cash in person.

I personally don't have enough funds to come out of pocket.