If you manage it yourself, tenants likely manage simple fix themselves.

You'll need a reliable network of local professionals (plumbers, electricians, handymen) you can trust.Hiring a Property Manager:Peace of Mind: They handle day-to-day operations, tenant communications, and legal compliance.Local Expertise: They understand the local market trends and rental laws in Colorado Springs.Cost: While there’s a fee, many find it worth the reduction in stress and time commitment.Lessons Learned from ExperienceBuild a Strong Local Team: Even if you manage the property yourself, having a dependable local handyman and a real estate attorney can save you headaches.Leverage Technology: Utilize property management software for rent collection, maintenance requests, and tenant screening.

As others have mentioned you start on Form 4562, but in my opinion you should have a simple google sheet or excel to track all of this for your properties.

A simple example is that they called to tell me the hose was left on in the pool.  

He apologized for the lack of communication.

All communications have to be through email, which is some cases is great, but in others it is horrificly time-consuming and inefficient. 

Any paper trails that should be in place or is it as simple as giving notice at the right time next year and not renewing the lease?

If booking direct and he has no reviews I would have him sign a simple lease, do a BG check, and have a reasonable deposit.

(to keep things simple)Property was primary residence for Person A from original purchase until 01/2020.

Turning a single-family into a multi-family is simple.