Comms certainly seems to be an issue doesn't it? The staff are passionate about the brand and work hard, I've had emails from my DS at 9.30 in the evening but there are certainly issues. They are a fledgling company and it does show at times. The handover process and QC is way short of where it should be.
Indeed, credit where it is due, even ~10 months before pulling the trigger the crowd at Bluewater in my case has been nothing short of amazing, basically insuring they do whatever they need to do to get me to into the car I want, the same story for my DS, and subsequently the ServiceCentre. Constantly amazed at replies to emails sent within minutes after 11pm and even after midnight, I cannot say I have had that with any other manufacturer of anything, ever.
As for comms, speaking to some staff on the topic a couple of months ago it appears that internal memo's are apparently circulated before press announcements, however seems like they are as confusingly-worded at times as some of the press announcements & blog updates we see, who knows if everybody keeps on top of everything, and in many cases of course, Elon tweets and the staff read about it on Twitter first before the corp-comms machine kicks in, so you inevitably have questions from buyers about products & changes the 'salesman' might not know of yet.
Whilst road tax and timings around the changes are a more local and legal issue, I am sure much of the same confusion kicks in - from the online clubhouse event it seemed clear to me that they would do whatever they can legally do to get as much through before the changes as possible (and geographically where possible legally), naturally some will be edge cases and be noisy about it however Tesla gains nothing by delaying your delivery. I somehow do not fathom Tesla requiring some fee depending on how the car is financed for keep-it-simple-stupid reasons but now I'm just speculating whilst mildly curious about the same
In reflection, having been in the roller-coaster of looking/order/wait/waitmore/delivery/post-delivery and just off of it, I suspect the comms are just about what I expect from a company doing ~20 production line changes a week and the "problems" that introduces with a CEO driving it all very hard from the top, it is not much fun whilst on the roller-coaster, but watching this sure is!