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.

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 career and auto investing in the s&p500.

It can be set to auto-classify trips as well.Best practice is to keep it up to date (i.e., classify your trips) frequently. 

It became everything from a drug den to sex trafficking to an illegal auto body shop.

The village, on the other hand, is totally destroyed.

In the free version it appears, at least by the way I entered them, it seems like it is auto calculating significant expenses for them but I am unsure of the assumptions or the way to edit these?

I've tried talking with some of the agents suggested by the auto-tool BP provides for "find agents in your area", (only 5 were suggested!

Good question, i'm not sure how the HOA will manage STR.The Villages is building a new community center & hospital 4 miles away, so there may be a market for it.

Compared to 2018, I am paying 6x the premiums on homes, on autos it's been more like 4x.