I think the dates also matter. Initially he was told delivery before Sep 30. Now around Oct 10. A clear difference.
Related to date - as Tesla doesn't have culture of negotiation and discounting, sales associates have no freedom to give discounts. So all they see are prices in the system. Current discounts are in the system (for cars produced and to be delivered in Q3), probably assigned by some data driven group in charge of delivering Q3 inventory push.
Problem this individual has may be as simple as getting to someone in HQ that can override price, or it may be more complicated.
Potentially, Tesla may be scared of creating a precedent, as there could be quite a few cars that may get pushed out. Worse yet:
Imagine (and this is just speculation), if this inventory clear-out has also a purpose of flushing the pipeline before change in production, starting October. New wiring harness, new sensors, whatever, something new, important is coming. Now, imagine word got out? Wouldn't it be a neat trick to place an order for Q3 with serious discount, and then postpone it, claiming some serious enough reason? I can see some people playing this game, perhaps not too many, maybe hundred(s), but amount of money at play is way over signing authority of some poor bureaucrat that makes choice to settle complain we discuss here. Perception is reality, and you know what newspaper titles are going to be, so question then becomes, what would Tesla do? Gives smart rascals that play game (order and delay) couple of $millions of discounts, or risk getting attacked in media, again!? So it could be ultimately a smart bureaucrat that's denying this request, one that cares about his job, though it makes him look heartless and makes Tesla look bureaucratic. Perhaps this situation gets resolved and guy gets his $3650 discount once we are in October?
Of course, this is speculation. I would not be surprised production change is coming though. If you get few Gs discount, can you really complain you missed out on the new hardware? This is a smart way to keep buyers of the last of old sensors happy.
And discounts are now present in Canada, but, it's a funny thing, cars that are discounted (75Ds), are discounted for the value of additional equipment, so there is still a nice margin for tesla there.