Treat the cost of those plane tickets and coffee dates as an insurance policy.  

When we were considering where to invest, and whether or not to self manage those investments, proximity by car or flights was a huge factor. 

You could sometimes have your primary homeowner's policy extend liability, but typically getting a standalone liability policy is the ticket. 

The real money is in scratch-off lottery tickets.

Go educate yourself on that, a plane ticket and a couple nights in a hotel might be the best investment you make all year.

Our goal is to not have to replace either of those large-ticket items as long as we hold the property.

I live next to a Delta Hub, and direct Flight to AK is still only one per day during summer ONLY and can cost $2K, or spending 10+ hrs to flight non direct (I could’ve flew to Europe with that much time) and vs right now if I need to fly to my OOS properties, it’s $200 on southwest. 

Because let's be honest, how often are you going to book a flight, a hotel room and rent a car to go visit your rental?

I have tickets to go to Mexico in November.I'm not planning to use them....https://www.nytimes.com/interactive/2020/world/americas/mexico-coronavirus-cases.html?

Does anyone have typical actuary schedules for useful lives of big ticket items.