We had a vacation home in Sunriver, about 20 miles south of Bend, Oregon. It is a marvelous place all seasons. It was a small house in a condo development, a 'Ranch Cabin."
Sunriver is a very popular vacation development in central Oregon. We put the cabin in a rental pool which significantly offset the cost of purchase and was more than enough to pay for maintenance & taxes. We sold it when the kids started college for a tidy profit.
What we learned is that as kids grow up weekends are consumed by athletics and Scouting. Driving 4 hours from Portland to Sunriver with a car full of kids is nerve-racking. And, as they grow older, we wanted them to have a variety of experiences. The fact that our cabin was essentially booked all summer and most ski weekends justified our keeping it.
I haven't talked to Sunriver rental agencies recently but my last conversation with them was that the big houses rented the best. We stayed in one a couple years ago and I noticed that they experiance a lot of wear and tear. Purchasers should rent a property they might buy for a week first.
Several couples in my building own vacation homes/condos on the Oregon coast. They can get there in about an hour and a half from Portland and they have children, grandchildren who also use it. As I listen to their coast house stories I notice that they started with a grand house, found it was more than they needed and downsized.