Realistically, we've had range issues only a few times last year, and by issue I mean we had to charge going and coming back. Only one time did we have to drive slowly to make sure we made it to a supercharger. Supercharger stops have been fun for me, so no complaints.
We have a cabin in Big Bear Lake, CA that I have to go to maintain consistently, but also enjoy as a get away. That trip is at the edge of the Standard Plus's range because of the elevation and distance. We also took the Tesla to Yosemite National Park, and that was the most range anxiety I've experienced, as once we entered the park we could only realistically charge at RV parks. My wife does not need range on a daily basis, as she commutes 5 miles.
I've wanted to take road trips with my family, and with the 500mi range of the truck, that will be much more doable. The Model 3 that we have would make us very anxious on a road trip for say CA to TX.
For me, it's both that ability to not worry about these frequent trips to the lake house, but also what you said about degradation. If it loses 20% range in 5 years, I'd like to start out at +500mi rather than +250 of the single motor Cyber Truck.
353 is a range that I would definitely feel very comfortable taking road trips with. I'm past one year owning the thing, and still love driving it.. so the honeymoon phase lasts for a long time. Especially with all the great changes I saw along the way.