My situation is: I'm single, I work remotely, income $145k and I really dislike the cold and am considering a winter-long trip touring Mexico, something I have wanted to do for a while.I think the best option for me would be to find a townhome at about ~$500-550k with 3-4 bedrooms, rent the rooms out and live in one.

Our only unit in Chicago had a pipe burst over the winter, and our current property manager has been a disaster getting repairs even started.

My main goal is to eventually set up a STR and allow for a period of time during the winter for my wife and I to travel down to unthaw from the cold and snow…however I’m open to LTR as well for the time being. 

Quote from @Rochelle Winters: I agree with Brent. 

@Albert Velasquez most folks who live in the western burbs will either gravitate back towards the city in suburbs like Brookfield, Berwyn, Forest Park or La Grange, or they will end up pushing further west to Aurora.

Since I consistently doubt myself I can't see the forest from the trees at this point as I'm about to sign the dotted line. the tenants will pay electric and water, there is no gas.this is a Midwest conservative state.

But, who is paying for the heat in the winter and A/C in the summer?

The winter time was pretty slow (as expected), and inquiries have picked up since spring has begun (also expected).. but I am still running into the same issues.

Compared to a broiler that adds up during winter. 

I used to go to Vero Beach every year for winter.