I could try getting in touch with some of the hosts in my town and/or reviewing some of their calendars.

Sure, we should discount the past few years to be conservative, but only looking at prices on Airbnb calendars is like driving full speed down the highway with your eyes closed 🙃 

I am currently in Nashville, TN but will be relocating to Chicago at the end of the calendar year.  

It's typically the second and 4th Tuesday of the month but I would check out the website calendar to see when the next one is.https://www.madisonreia.com/

 - Its on the BP Events and Happenings Calendar

Questions/Answers from you guysSo clear your calendars and bookmark this thread for details on connecting, but we're going to do it on Friday March 15th at 5:00pm PST (that's 8:00pm EST) and probably will be using Google Hangouts for this.

Let’s say we flip the calendar forward a year and half and now I’m mostly debt free.

I know when I purchased my property, the old owners paid a prorated tax bill for their time of occupancy during that calendar year (2016).

You can discuss with them just what services you'd like them to manage - everything from complete management, to just managing the calendar, etc.I'm a co-host in Seattle, and have helped a handful of people manage their listings.  

http://mig.clubexpress.com/  and check out the calendar for the MF group.