You can certainly decide that. Some are very able. Also many don't care at all about such things. I too have areas in life where I really don't care about such things and I couldn't care less if the thing I get becomes old the next day. Unfortunately cars are not one of them.
I'm just being realistic. I have enough purchase experience behind me to know that the buying satisfaction - for me and many people like me - does take a hit when a product type we care about is replaced with a new one right after or even before taking delivery. TMC certainly is full of people like that, it is just human nature. So people like me plan carefully and try to time our purchases to get the latest for those products. I will look at when a manufacturer is refreshing a model, when their refresh weeks in the calendar are, and all that plays into my decision... With Tesla that is pretty much impossible, though.
Six months later... a year later, that's nothing. Who cares. It's the immediate period, that's the emotional part, because it ties into the whole experience and will have a lasting impression on how successful the purchase has felt. We all know technology ages, but if it ages already in that period where you're just getting grips with it, it can be emotionally unpleasant.
I got it right on my Model X, it is quickly approaching that six months old and has more features overall, discontinued particulars I like and was much cheaper then the Model X currently on sale. Eventually HUDs and whatnots will render it obsolete, that's normal progress. That's OK, it was in the end as well times as a Tesla buy can be. But this is becoming quite rare and hard to do with Tesla to get that six months. With the Model S non-AP, with the long delivery times I got it a few weeks after AP1 was launched. It was OK because I was aiming for the Model X anyway, but certainly it would have been nicer to be able to plan for such a thing.
With a German, pfft, it is simple to plan for a successful "honeymoon" period and extremely rare and unlucky to fail if you know what you're doing and have the patience to follow your own advice. There are basically certain weeks in a year to order and also certain sites to follow to get a good idea when a refresh is coming. That is useful in as big a buy as a car.
So, Tesla's policy - in the end - is making me reluctant to buy another. I know myself, why take the risk with such a big investment. Without a clear model-year type of upgrade point or usual refresh/facelift type of visibility into Tesla's roadmap, the tools we have for planning around this are very limited. It does not mean I would never buy a Tesla (certainly I've bought two), but it means their policy is creating a perpetual Osborne effect in my mind. The threshold for pulling the trigger again is getting higher.