Depends on the big question: what will it cost me?
But cost aside, probably not. I don't have that Apple plan. I find that Apple sometimes offers the product I want, and sometimes not. When they do and I buy it, I have the expectation that I'll hold onto it for 2-3 years, or even longer. By then the latest version feels more like a real upgrade. There's also a significant switching cost in moving over to a new phone, even with iCloud. Last time around it took me most of a day to get everything right. I don't really want to do that on an annual basis.
Cars are similar for me. I've hung onto the same car for years, partly out of inertia and partly because no one seemed to make a new car that I wanted to own. Maybe one year Tesla offers colors and interior options that I like, and the next year they're using the ugly brush — pardon, appealing to a different taste. Switching cars is, if anything, even more of a time sink than switching phones. I'd have to update my registration, insurance, and parking permits. I'd have to fiddle with settings that Tesla's cloud doesn't copy over for me. When they change the charging cable (hi Apple!) I have to figure that out. No, I don't want to do that every year.
Anyway I misdoubt this is the direction Tesla's headed in. If the Tesla Network means you can turn a profit on transportation as a service, I expect most Teslas will end up in the hands of fleet operators. They'll replace some portion of the fleet every year, of course. And maybe you can pay a little extra to ride in a new-ish one.
