We are curious to hear what creative ways more seasoned investors than us would do as a first move looking back on some of your first deals?

Hi @Michael DallasEnjoy the memories you are making as you enter your senior season!!

With reduced supply this could have a positive affect on rental revenue this upcoming winter season for short-term rental owners of homes that were not negatively impacted by the storm.

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 make sure whatever property I am looking at will do well based on seasonality.

BiggerPockets is full of resources designed to help you along your journey, whether you are just getting started or a seasoned investor.

Even better news, we can now offer No Seasoning on DSCR. 

Chicago for sure has all 4 seasons, but the winter helps us appreciate summer more lolI don't know zip codes off the top of my head, but some of the prime neighborhoods are Lincoln Park, Gold Coast, Old Town, Lake View, Roscoe Village, Wicker Park, Bucktown.Hope that helps...if you want to link up and talk more let me know.

I have the BP one but am looking for ideas for any changes or additions that seasoned landlords like to include.Thank you!

However, the short-term rental market comes with added complexities like managing turnover, dealing with seasonality, and ensuring you comply with local regulations.