Windows has had this incremental update challenge for years... Sometimes you perform updates, only to find another set of updates become available and are then required, and so-forth. I suspect Tesla has this whole distribution challenge understood and we here can only speculate ... but IMHO, if I were the one creating the process and were forced to make a choice (as I used to sign-off in former lives for other software), I would prioritize optimization of the update process to those users that were more current, and just maintain a process to catch stragglers up -- even if that then took more time or more interaction by the end users.
Again, I'm not pointing my finger at people that have elected to stay on old releases, it's each owner's decision, but not mine as I bought into my MS recognizing there would be both good and bad of Tesla evolving my UI experience. I do agree though that it makes support harder the further someone gets behind in their MS software updates (I'll reference again the Windows, smartphone, server and mainframe analogies). SC Techs (just as my old field computer service techs) cannot realistically be expected to not only do problem determination on a vehicle, but then try to understand the nuances of software releases on what they need to repair or replace beyond anything other than a very high level -- it's simply too complex to deploy that sort of approach out to the field if a company (and Customers) expect repeatable, successful and cost-effective repair actions, no matter what Customers may want. Customers can stay on old releases for a time, but as has been said, their day of reckoning will happen when some sort of SC repair is required.
...and I agree Hank, as some of us have said ad infinitum in various threads, as the fleet grows, Tesla (and Elon) must do a better job of not just doing what they always think is right, but have a real advisory council providing input representing a cross-section of true owners -- not just Sigs, techie-types, etc. That is the only way to successfully grow into a volume market while maintaining customer satisfaction. Future potential buyers and owners (esp for vehicles like M3) are not going to want to be the bit twiddlers or techie-types many early adopters are, nor will they appreciate having changes happen to their UI without advance notice and understanding. The masses simply won't accept that part of the approach Tesla has taken to-date.
