Of course have no clue to his background in RE but it seemed to me on the surface this was a new venture for him and it certainly looks like he got over his ski tips.

IN 2005 there was a builder in Vancouver WA who got over his ski tips and built 25 duplexs all at once but only sold 5 in 6 months and their bank was hounding them..

One thing I try to remind myself is that enforcing a lease is a LAST RESORT not a first option.

Using that space would be a last resort, but it is an option.

After multiple attempts over the course of weeks we will eventually resort to changing the locks.

So far, I've checked SunDestin, Destin Seafarer and Pelican Beach Resorts, along with a few others. 

However, there are some challenges to keep in mind:Regulatory Variations: Regulations can vary widely between locations and are constantly evolving.Active Management: STRs require more hands-on management for guest turnover and communication.Additional Costs: Don’t forget about expenses for furnishings, cleaning, and possibly hiring a property manager.If you’re looking for STR-friendly areas, consider these locations, as others can be too expensive to consider, such as Snowmass Village or Aspen:Breckenridge: The most visited ski resort in North America, attracting around 3 million tourists each year.Steamboat Springs: A popular year-round destination for winter sports and summer activities.Keystone: Great for those wanting a less crowded resort experience.Divide & Florissant: Charming mountain towns close to Colorado Springs.Fairplay: Just 30 minutes south of Breckenridge, with an impressive 82% Airbnb occupancy rate.Cripple Creek: A former mining town now known for casinos and outdoor activities.Park County: Very Airbnb-friendly, though regulations may change.Here are some strategies to help you succeed in the STR market:Hybrid Model: Consider using some units for STRs and others for long-term rentals to balance income.Research Local Regulations: Always check the current rules in your target areas before investing.Year-Round Appeal: Focus on locations that attract visitors in all seasons.Quality Furnishings: Invest in quality to justify higher nightly rates and attract better guests.Dynamic Pricing: Use pricing strategies to maximize revenue during peak seasons while maintaining occupancy in the off-season.Stay Flexible: Be ready to adapt your strategy as the market and regulations change.While Colorado’s STR market offers exciting opportunities, it’s essential to approach it strategically.

I could find people fairly easy.Add the excitement of a hurricane off the coast (resort shut down at 9 PM so workers could safely get home). 

The property has a resort feel and would be a great STR. 

Hey @Ruth Reyes, I agree with both @John Underwood AND @James Carlson.I never really look hard at condo's due to the HOA fees and the fact that a controlling member can rule the roost.For example we almost bought a ski condo at the Inn of the 7th Mountain in Bend Oregon.