I think it is great that Tesla is doing this and I wish that other, lower base cost, manufacturers would do the same. Everyone is different and has different driving needs. So let the consumer decide how much battery they each need. I think the adoption of EVs would happen a lot faster if we didn't need to spend all our time talking about the range limitations of 100 miles.
Another thing to take into account is that what a cycle does to a battery pack in terms of life reduction is a function of how deep that cycle is compared to the total capacity of the pack. So people who invest in larger packs are going to see their packs last longer, given the same driving cycle. This may allow more people than you might think to invest in a bigger pack. There is a penalty in terms of greater energy consumption to drive, but there is also a benefit in greater battery life. And possibly the elimination of a whole other ICE car.
Naturally these issues will eventually go away as batteries get better. But for now they are important.
I think what will be more interesting is to see how much range people pay for in their second EV. Initial purchases will mostly be based on guesses. Nobody has ever had the choice of a 300 mile production EV before.