I faced a similar problem and ended up creating custom designed Excel spreadsheets that auto-populate with each other.

I have some auto-denials in the "review phase" based on landlord reference such as numerous late pays on rent, numerous documented lease violations, and move-out damages exceeded collected deposit... but still have yet to enter the "landlord reference/review phase" of my screening process due to the details on their CBR's as noted above. 

These will auto-categorize transactions for you and saves a lot of time. 

Depending on the extent of the damage the City/Village might condemn the property and force you to tear it down if you let it sit to long.

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.

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. 

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

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