No offense, but for someone looking at a 90 unit apartment building which I'm assuming you will be syndicating to raise money for, this seems like a question for someone who is out over their skis a bit.

Although it's much more popular in the summer and you can get more money for rentals around that time, you're still getting people in the winter because it's so close to ski resorts.

Especially in affluent, resort communities.Workforce housing is best solved by the private sector not the public and taxpayer.

but then there was an RV  in the driveway new cars maybe a boat or jet ski.. it comes down to money management skills.. tenants are no different in many instances.

This client bought a big one in Florissant -- not exactly a well-know resort town -- that's going to make about $115k/year gross. 

But Central Oregon is a prime example hard to develop .. but huge carve outs for top end Golf resorts  cant build them like that anywhere else in the state Because of zoning..

We built the Estancia nightly rental resort condos in St George, UT for an investor that sold units to individual owners.

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.

If you like skiing, then buy in Park County (Alma or Fairplay are the cities), which is just south of Summit County.

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