I don't think I've ever been reached out to by any individual at Tesla; all the communication has either been initiated by me or a system-generated message. About 3/4 of the time when they say "we'll get back to you" they don't unless I remind them once or twice. When I've reached out for information the responses have been terse. I'm asking for something a little unusual (factory delivery from out of state); my sense from the folks in the process is that they view this as a pain, not one that quite meets the standard of them saying directly to me "you are asking for something unreasonable that we are not interested in fulfilling" but one that it appears that few of them have the time, energy, or interest in supporting... their emails do a good job of conveying the message of an eye-roll emoji through their text.
The message I've received in a nutshell is this - yes, your VIN has been assigned (58xx); yes, the system says you're late-April to May; no we don't know when you'll actually be delivered; no we don't know if it's actually in production; we'll tell you when the car is completely done and ready for pickup and not before; at that point you better hustle your way out to California because we won't hold the car for long; and no, we won't give you anything further to go on to buy plane tickets - you'll only know when the car is completely done and ready for pickup because we don't want to be accountable for any slippage in the delivery schedule.
So, to answer OP directly, I don't think the system is set up currently to proactively inform customers of much of anything. Actually, I don't particularly fault the individual DS's involved; it appears to me that the way Tesla is handling the revenue side of their business is to understaff and, I would speculate, underpay their service team. The overall organization is young, green, and feels to me populated with a "startup bro" culture rather than with a mature, professional, service culture. I'm not even that frustrated or pissed off; at this point I think it's kinda comical, really, to compare this experience to what I've seen buying BMWs either through a dealer or through performance center or european delivery - it's such a different experience it's as if they were completely different product categories.
Given Tesla's short history and cash flow I'm not sure I can disagree with their choice from a business perspective - capital is expensive, cash burn is off the charts high, and scaling up engineering, production, and the gigafactory have to be top priorities for investment. Their PR efforts appear to be paying off in terms of long reservation queues. Bleeding edge early adopters like us are willing to accept a Walmart service experience at Nordstrom prices and even offer indefinite duration zero interest loans because it's part of the early adopter "tax". Given that, why invest in the sales / on boarding process at this point? But if they're actually going to fulfill their promise as a global premium car company over the long run, they'll have some rebuilding to do.
