I live outside Chicago and recently drove to Florida & back in my Model X 90D. On the route down to FL, I charged in Lafayette, IN and wanted to get to Louisville, KN, 183 miles away. Similarly I later charged in Franklin, TN (just south of Nashville) and the next supercharger is in Birmingham, AL, only 177 miles away. Both of those seemed well within reach. I left Lafayette with too much confidence and was driving about 80mph when the X warned me I might have trouble getting to Louisville so we diverted to the supercharger in Indianapolis. I might have made it fine, especially if I slowed down, but range anxiety kicked in and I didn't want to risk it.
Unfortunately there is no intermediate supercharger between Franklin, TN and Birmingham, but there are lots of rolling hills. Again I wanted to drive 7-9 mph over the speed limit but it was also cold and the winds were strong and there was a bit of rain as well. As my 90D crested one hill in particular, the 90D told me I was in now serious trouble (not just a little trouble). With no option for an intermediate charge, I dropped my speed significantly and drafted behind a truck for about half the trip.
With a 100D, I think I would have had the confidence to make the Lafayette-Loiusville trip with no problem while driving "normal" speeds, and it would have also made big a difference in driving the hills of TN as well. I would gladly pay $10k now to drop the battery I have if I could upgrade my battery to eliminate that range anxiety and let me drive just over the speed limit rather than well below the speed limit.
Don't think that range anxiety only kicks in for trips of 200+ miles. It kicks in even at 177 miles, at least if you want to drive the speed limit or just a little bit more. If you ever plan to take any road trips, pay for the largest battery you can. If you're only going to drive near home, then get the smallest battery. That's my 2-cents with 2 real-world examples.