Should I schedule or wait?

I have an upcoming flight for a vacation and I’ll need a ride to my rental. The airport is about an hour from where I’ll be staying, and I’ll need the ride around 9pm. I don’t mind paying more for a scheduled ride; I also don’t mind tipping well (I’m thinking $20 but let me know if I should do more). I just wanted to ask because I’ve seen on here that scheduling doesn’t always go well, but I’m scared to wait till the last minute. I just need to know for sure I’ll have a ride.