Glad to join the site here and looking to connect with people in regards to networking, working on business and any questions concerns people may have. If I can be of benefit to you in any way don't hesitate to reach ...

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 have a friend who’s an attorney and had over 25 rentals at one point.

Hey there! I am newer to the Real Estate Investing community. Currently have one rental and looking for my second property. I have been working with a realtor in the past (when I bought my first property) who does not...

@Shawn McMahon I will echo that getting connected with a good real estate broker will make things easier, but meanwhile the Redfin.com app gives you the next best access to MLS listings, and is a little more user friendly than the MLS Portal.  

These loans usually consider the property's cash flow more than your personal income/credit.2.Switching to an LLC: Transferring your property into your LLC can offer asset protection, but it won’t necessarily make it easier to get future properties unless you're using LLC-friendly financing.

- Are these areas rental friendly ? 

My municipality has turned from being STR friendly to STR hostile.  

My target markets are NY and CT, but I’m definitely open to expanding my horizons.Since most friends and family members are hesitant about real estate investing, I'm on the lookout for a mentor who can guide me through this journey and potentially partner with me along the way.If you have any advice or know someone who might be willing to help me get started, please let me know!

I did just broker a .9% deal I sold off market in Chicago and this is a good area with $1400+ rents a unit so making friends with realtors and having them send you stuff before hits MLS is an option too.