Real Estate is a team sport. 

I would ask for the last few years of the Tax Return Schedule E for this property to see what their total expenses and net profit was.

Quote from @Scott E.: Great post Jake.

Hey Everyone,I’m the co-owner of a small production company focused on Esports and Gaming content, but I’m diving into real estate investing and fascinated by the intersection of video marketing and property sales.After doing some research, I’ve noticed the pricing and usage for real estate video services can vary wildly—from $100 to $5,000 for anything from basic photo packages to full video suites with drone footage and social media clips.I’m really curious—how does this align with your experience?

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.

It's like buying a Yugo and then complaining it doesn't drive like a sports car.You ALWAYS end up getting exactly what you PAID for!

Quote from @Scott E.: If I read your post correctly, you are currently running your guest house as a STR, but you do not currently have proper insurance in place.

Also looking for R E Agent / Investors form out of state to give me some insite of your market. 

I entered the market after a successful e-comm business sell out with $80k.

Stop hanging out with your deadbeat buddies who spend all day drinking, talking sports, and otherwise wasting away.