@Paul De Luca i have tje chicago standard lease, no additional language.

This is how you de-risk a remote investment.Speaking of which, I noticed Min Zhang also commented on your post.

This is going to be very situational like @Paul De Luca said check with any HOAs then check with the city, county, and state to understand how the laws would impact you.If you are in the Chicago Metro I imagine you have this happening all over the place.Maybe try talking to an attendant at one nearby and see what they run into.How many spaces are you planning to rent?

They check that all the light bulbs are working, TV remote, etc. etc. 

Use short, benefit-focused lines and highlight unique features (“Close to downtown,” “Perfect for families,” etc.).3️⃣ No emotional connection – Most hosts sell features (beds, Wi-Fi, TV).

This included changing cleaners, changing plumbers, changing HVAC companies, tinting windows so they don't look as dirty and need windows cleaners, changing internet providers, changing from satellite TV to DirecTV stream, remove/change items requiring high maintenance like skeeball along with a dozen other things. 

Quote from @Stephen De Vita: Hello,I am on the look for a CRM.

I have purchased rural land where I built my home (I have the land with an acta de posesion not title), and I am looking at other opportunities in this area.

@Paul De Luca would love your insurance agent contact, thanks! 

I'm 43 and own an ~$850k condo in San Francisco (primary residence, year 3 of a 7/1 ARM @ 3.25% with interest only payments) and own a ~$600k condo in Delaware that I manage as an STR during the peak season and as a 6-month leased property during the off season (purchased in 2020, 2.875% 30-year fixed).