First of all, I am sure there are some key learning opportunities you took away on properly vetting tenants and figuring out the Chicago Landlord-tenant ordinance (i.e, move-in fee).I'd just talk to your tenant first and see if he can be reasonable, then resort to cash for keys.

We have a top 10-12 resort style communities that are geared for this exact thing and then a couple dozen others depending on the style/size of home and type of amenities you want out of the community. 

Based on the other replies the math probably won't work for a small investor, so I'll probably wait for the next downturn to get some cheap 2nds when there's too much debt for the bigger players to gobble up themselves.

It is located in Pagosa Springs, CO; sort of a touristy place south of Colorado with ski resort about 30 minutes away.

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I am a real estate broker living in a resort mountain valley in Colorado (Vail).

@Chiara Poderi We are not players, we are property investors. 

I know the bigger players aren't looking for 20 units and under etc.

A lot people are moving here because they can feel at home without being confined into any apartment or resorts.

It’s located in a popular Air BNB resort area with a great school district.