To answer the original question --
I asked myself something similar, first when my initial lease ran out, and I had to decide what to do. I bought my car because I liked it and it had been reliable, so I figured "the devil you know," etc. I could have found a newer used car, or bought a brand new one, but did not feel the extra cost was warranted by the potential benefits to me.
The Model 3 does not particularly appeal to me, mainly because of its smaller size. Plus, I am quite happy with the performance and features of my Model S. I have leather seats and a sunroof, neither available any more. The AP1 performance is solid, better for now than what the AP2 seems to be doing. I know AP2 will catch up and eventually be better, but for the moment at least I am quite content with what my car can do. I have no need for or interest in the video games. It would be nice if the computer were a bit faster, but again it is adequate. Some of the features of the Raven versions are attractive, such as the enhanced air suspension and the better audio system, but nothing is so compelling that I feel that my car is outmoded, and I feel no lust to get a new one.
Then I thought about this choice again when my warranty ran out. But this Tesla was my very first new car, the only one I have ever owned in 50 years of driving that had a new car warranty. So, I was not intimidated as much by driving a used car without a warranty as some folks are. But before too long, I decided to purchase the ESA, so I suppose I was hedging my bets, partly because of the risk of the computer failure but also because there are any number of other costly repairs the car might face in the next 4 years. Full disclosure: I live near a service center (Dedham) and have had very good service there. Plus I am retired so I am not quite as dependent on my car as some people would be.
Everyone has to wrestle with this choice and decide on the basis of their own needs and value criteria. So far, my 2015 Model S is still a great car!