My biggest piece of advice is to get a killer rental agreement/lease for Cook County.

Clients now only use what they need & not much more.We have it duly written into all of our Leases, so it's fully disclosed and we engage all prospective Tenants in an honest conversation about paying all of their bills before they move in. 

A month ago there was a very tramatic event in their family where they asked if they could get out of the lease. 

You should use the same lease agreement.

These are the options we're currently thinking of:Option 1: Sell the house that we most recently lived in when the current lease is up in June.

My STRs are in a small destination mountain town and finding good cleaners is the #1 struggle. 

Something isn't quite adding up for me:-New builds selling for under 300k-4 bed 1800 sqft SFHs are leasing for ~$2500 / month with with less than 30 DOMThe dissonance comes from the rent:price ratios and asset quality.

They may make unreasonable complaints about me and then I find myself patiently explaining the terms of the lease again and why things are the way they are.  

We use Innago which allows my tenants to sign leases, send rent, and fill out applications for free. 

Guests want to come by early, surprising my cleaners or wanting to drop luggage off early.