I self-managed my first rental because hiring a property manager felt like an unnecessary expense for one unit. That part of the decision was right. What I didn't expect was how much of the job is just remembering things, at the right time, without a system that reminds you.
Nobody warns you that a lease renewal window sneaks up on you, or that the maintenance request you meant to follow up on gets buried under three newer emails, or that "I'll just remember to check if rent came in" works fine until the one month it doesn't.
The actual skill of self-managing isn't dealing with tenants, which is mostly fine. It's building a system, from scratch, by yourself, for keeping track of a dozen different small facts that all have deadlines. Most first-time landlords build that system out of a phone's Notes app and hope. I did too, for a while.
The thing that would have saved me the most stress in year one wasn't advice about tenants or leases. It was just having somewhere everything lived: every property, every lease date, every maintenance request, every payment, in one place I trusted, instead of scattered across texts, email, and memory.
You'll figure out the tenant stuff. Build the tracking system before you need it, not after the first thing slips through.