I have a Vrbo lake house and I was pleasantly surprised how much it rented in the fall, winter and spring.

There is a $10 cap which wouldn't be awful if he just sent one invoice per customer but payments are often broken down in to 2 or 3 payments over the winter season so we are looking at fees that could be $20-$30 per week of rent. 

Partly to change the furnace filter and stuff like that (show him where the water shut-off is to the outside faucet so the pipes don’t freeze over winter) but also make sure he hasn’t done any unauthorized work on the condo. 

Dumpster rental, electrical bills to keep the heat on during winter so pipes don’t freeze, man labour.

I’m not much more connected and knowledgeable about Chicago as I am elsewhere, alart from knowing that taxes are high, winters are brutal and population is decling every year.

We have a great meetup that meets the first Saturday of the month in Winter Park.

I then ripped out the remainder of the swing set and cleaned all debri that had accumulated from the winter in the yard. 

Good news is that IMO rentals are more plentiful in the Fall and Winter months (at least they have been for me).  

Near the end of 2017, a forest fire burned down my property along with about 300 other homes in the area.

I'm already planning what my winters look like because I want to spend them traveling to other countries, I'm fairly close to having my business automated to the point where I can choose to shut it off, and turn it back on.