Glasses seem like a stretched analogy. Unless you make it a point of keeping your sleeves rolled up so everyone can see your watch (or god forbid are a double-wrister)
what better way to stick it to the man than to buy used at a big discount to used (at least on the striking time, don't know about the RL) and getting all the enjoyment without contributing to their bottom line? in all seriousness though if you want it you should get it i don't see why you should de
i wouldn't necessarily view subsequent generations being unequivocally better (these are atavistic ornaments, not smartphones). Even if the movements might get 'better' (longer power reserve, instantaneous date change), they're often paired with design or size changes that you may not care for. i.e.
Next year is the 25th anniversary so i suspect that there will probably be some kind of likely limited edition colorway / design, offered, but not clear to me whether they'd discontinue the current line.. Nevertheless, i think it makes sense to wait assuming (i think reasonably) that you can look at