It’s about 1/2 hour away from Fond du Lac and West Bend, which are the 2 biggest cities nearby.

What’s your biggest question or concern about diving into the market here?

Biggest things are to make sure you get a very thorough inspection report and make sure you have very reliable contractors.

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.

My biggest problem with all of this is the constant undermining of hosts by the two heavyweights.

My biggest concern with blue ridge is cleaning companies and handy man services. 

I joined J&G for a lot of the same reasons already mentioned, but the biggest one was I felt that they were genuinely interested in my success as a student. 

For those who have been investing in rental properties, what are the biggest financing challenges you've encountered, and how did you overcome them?

Honestly, i'm not the biggest lover of being in the city..

What was the biggest mistake you made when you began investing in real estate?