I just joined the BP community and thought I would add in my personal experience on this topic. My husband and I own a 1BR/1BA ski condo in Keystone. We live in Kansas City, so we pay a management company that handles all of the details like contracts, payments, cleaning, maintenance, keys, etc. They book some rentals for us, but we get most of our bookings from VRBO. We put about $10k in for new furniture and upgrades when we purchased. Net of commissions we cover about 75% of our costs each year which includes the $350/mo HOA. Season is Thanksgiving through end of April depending on snow. We book a solid 100-125 nights during the ski season and only 25-50 nights the entire rest of the year (mostly weddings in July/August).
If you are looking for a positive cash flow on this type of investment, run. Run fast! My advice, don't go on the cheap if you really want to maximize rental income. Concentrate on location and make your unit stand out in the pictures. You would be amazed how many people book with us because of the trendy red couch in the photo!
If you do purchase, look to do it April - November when inventory is higher and owners are not getting any rental income. They are less likely to negotiate a sale when they are getting ski rental income. Many take their properties off the market during the ski season and put them back on sale in April when rental income dries up.