So I have a rental property with two fairly mature trees directly in front of it. 

I don’t think you have to worry about any expenses maintaining it because it’s on your land.

What is customary, what is expected, fair, etc. ?

I moved in to rental in NJ 7 months ago and I am in a fairly unique situation where my landlord has become a mentor of sorts.

However, it’s important to maintain enough liquidity for unexpected repairs, vacancies, or other expenses across your existing portfolio.If I were in your shoes, I would likely lean towards reinvesting in a way that balances both cash flow and appreciation.

Consequently the students do not fair so well.

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.

Fair points. 

Once those steps are done, the process becomes fairly straightforward.If you’d like, we can send you a copy of our Section 8 Guide for Landlords, which goes into more detail.

When it comes to tenant screening, it's important to balance your right as a landlord to protect your property with compliance with Fair Housing laws and local regulations.