We just got back yesterday, and I figured I'd post how it went down for posterity.
We stuck to the ABRP plan on the way to Colorado, and we used the in-car nav on the way back home. I think the in-car nav is better for our family because it tends to prefer fewer, longer stops. I think that works better for us, even if it is a few minutes slower over the course of the trip. There's a certain inertia to doing anything with kids, and all transitions take way longer than necessary. So once they're in the car, it's better to stay there, and same for making stops. While trying to follow the ABRP plan, we regularly stayed at a stop longer than required just to get everyone moving back towards the car.
As for the accuracy of the estimates:
I haven't given ABRP access to my Tesla account, because I'm just a little too paranoid about cybersecurity to do that. As such, the ABRP estimates were regularly too pessimistic with my actual car model selected. I switched to planning for aero wheels (263 Wh/mi reference consumption), and that seemed roughly correct.
The in-car nav was overly optimistic. By my guesstimate, we used 1% more than expected for every 10 minutes. So if we were doing a 2 hour leg, we needed an extra 12% charge, compared to what the car thought it needed to get to the next stop. I was regularly driving 10 over the speed limit, so I'm sure that was a contributing factor. I really wish I could tell the car to plan towards that.
All in all, the trip went well. Thanks to all who answered my initial questions!