For example, Chestnut says: "improved power management", will all previous models get that?
In Birch it says "Next run of board", are there changes that change the software in any way?
Evergreen is the "LTS" release, do the others not get "LTS"?
In Q4 2020 there's a new CPU, does that affect drivers or software in any way? Will they provide software updates for all devices for a number of years?
You'd hope opting for Model 1 2019 doesn't punish you but I can't see how they have the resources for testing every single model for every single software release.
It's not a good idea in the long run. Not even Google would do something like that and nor should a smaller company, it's idiotic.