This is ideal if you have a full-time job or don’t want to deal with day-to-day landlord tasks.✅ Professional Tenant Screening – Property managers have systems in place to screen applicants thoroughly, reducing the risk of bad tenants.✅ Knowledge of Chicago Rental Laws – A good property manager stays up to date on local laws, helping you avoid costly legal mistakes.✅ Maintenance & Repairs Handled – No more emergency calls at 2 AM about a broken water heater!

A good company will have you fill out some easy online paperwork asking you some details about the doors, and they can get you transitioned into their system in 1-2 days, including reviewing your leases and notifying tenants about the change in management. 

Last short term rental we put on the market was booked for a 30 day stay first day on the market.

You’ll have 45 days from your sale to identify them and you’ll have to buy enough of them, and only them, within 180 days of your sale to meet your 1.1M requirement, or face taxes.

What do you do to relax at the end of the day? 

Even if you get something in escrow right away, it's still a 30-45 day escrow period before you would get paid, unless you are working with cash Buyers.  

It's rare that you'll find a good seller for #1, so the only option remaining is to document the condition from the day of purchase.

We are starting to hit our capacity with pulling data from reports and running some of the day to day operations.I would like to know what key people we need and if we’re analyzing the right data.

Is it true if I rent it out on Airbnb for at least 2 days before the 100 days are over, I should already be grandfathered in?

We rarely have issues, but it seems like such a small investment in time and money to take one day to verify.