Hey @jordan - In Illinois and specifically Chicago / cook county you never know what is going to happen with property taxes. 

google steve cook.

Great very rural place.. built in 85.. over all good condition, HVAC looks good only one broken window pane.. roof needs work.. needs gutters and new floors and new kitchen counters.. and a couple of closet doors.. oh and popcorn removed and painted.. had been occupied by heavy smokers. 

.)- Tenant operations that may be harder to insure (cooking, woodwork, manufacturing, etc.)- Construction of buildings/fire protection that may impact the insurance (frame construction in a non-hydranted area or one with distant fire depts)I echo the posts that emphasize the importance of an experienced real estate attorney. 

In addition Cook County has set up few new classification for properties that are converted to STRs. you can visit the assessors website to find oit more.

I am usually working till about 9:30 in time to cook diner, watch a short Netflix show, and hit the hay. 

You will find hype, unrealistic expectations, and half-cooked advice (sure, like mine).The BP books are so so, not great.

Both Airbnb's and hotels have their places in the market, though I do agree that I've seen more people shift their travel towards Airbnb as bigger groups can often make travel much cheaper by renting bigger houses while having separate bedrooms, being able to cook is often a huge plus as well. 

I love listening to the podcasts cause I can do it when I'm cooking, cleaning, driving and so on. 

The next information is extra and I don't know if I should add but, methamphetamine was cooked in this home and a person died on the property as well, so there is the possibility of drug residue inside the home.