Ultimately, this method of doing business is doing us a disservice and will hurt resale values over the long term. Thing about the Model S 40kW, 60kW, 60D, P85, etc- all of which had significant resale value hits when those models were discontinued.
I definitely agree that replacing a model with an improved model (cheaper, better, or some combination) hits the resale value of the old model. I understand it hurts to buy the latest and greatest, and then see something else you want. I don't mean to dismiss your concerns.
But the resale hit only comes if the new model is an improvement. I think the 40kWh is a great example - its value didn't go down when it was discontinued, it went up; people were selling those for near-60 prices. Because it wasn't replaced with anything better or cheaper. Discontinuing models isn't the problem; improving them is.
Even there, the biggest hit happens when the top dog is unseated - but that only happens once; all cars get upgrades; and resale value doesn't matter until you sell - add them all together, and none of this makes much of a difference unless you resell your Tesla after they have upgraded it but before another manufacturer would have upgraded it (actually even before then; those last few months before a new model comes out are killer). There is some hit to resale values doing business this way, but I don't think it's much different than what happens with gas cars, it's just that the big ouch comes sooner.
More importantly, the better Teslas and EVs get, the more people are going to want one - and Tesla can only scale their assembly line so fast. If EV adoption is like most types of technology, we are likely to hit a point where suddenly everybody wants one, but there is not enough capacity to build them all - then used ones are going to gain value. The best way to get this scenario to happen is to make everybody
want an EV, and constantly building better ones and staying in the news until it's clear to even casual observers that EVs are better is the fastest way to make that happen.
I do not think Tesla should change their fast pace of innovation. My Roadster was long ago supplanted as the EV king by a faster, cheaper, more comfortable, 5-to-7-seat, high-tech, Supercharge-capable, AWD Model S. But it is still the same BLAST to drive that it was when I bought it, and I have no regrets at all about buying it. Not to mention I think the lost value is pretty comparable to that of, say, a Porsche 911 Cabrio which retailed for about exactly the same amount. It lost a lot when the Model S came out, but has held pretty well since then. In fact, with Tesla updating old models, it looks like the value is even going up a bit (we'll see for sure after the Roadster 3.0 announcement).