Assuming there were no other manufacturing or market factors at play, I can see why Elon made the statements that he did about 244 miles of range...
Before my Model Y LR we had leased a couple of BMW i3s (in sequence, over the course of 5 - 6 years). The first had 80 miles rated EV range the second had an updated battery with 120 miles of range. Both had range extenders (essentially an onboard gas powered generator adding ~50 miles of range) as a very necessary safety net.
While ok for running errands, and strictly for around town use (which is all we wanted it for) 80 miles was very low and there were many times we ended up relying on the range extender to get us where we needed to go with that car. The 120 mile version of the same car actually made a very significant difference (even though it was only 40 miles extra) and over the course of that lease we very rarely would end up having to use the extender. It was sufficient for around town use, but still not practical for road trips, and while it could have worked for someone with a longer commute, it would have involved relying significantly on the range extender maybe on a daily basis, which would kind of turn it into more of a hybrid for that use case.
One of the things to consider is that with EVs there are multiple factors that can affect the actual range you get. On a car with higher total range this will not matter as much for the average user as they will have ample range to play with for day-to-day use. If a car has lower range, it starts to matter more.
244 miles is actually 220 miles when charged to 90% (max recommended daily level of charge). Additionally while I live in SoCal and have not had to deal with this personally, I understand that the ambient temperature can have a large effect on range with the range dropping significantly if the battery pack is extremely cold, and finally there is normal battery degradation over the course of several years. Adding these factors together, that 244 might become something more like 180 - 200 miles average real world range after 3 - 4 years of use.
While 200 miles is plenty for around town use, based on my own experience with the i3. It could start to become problematic if someone was actually banking on having the full 240 or even 220 miles of range available to them on a daily basis due to their commute.
Given Tesla is trying to sell the Model 3 and Y as direct competitors to mainstream ICE cars, for the average John/Jane Doe ICE driver who is trying their first EV, having a max of 244 miles of range could create scenarios where they end up feeling like they were duped into getting something which cannot meet their daily needs. If bad enough, the experience could be enough to turn them off of EVs for a long time (the opposite of what Tesla is going for).
This is not exclusive to Tesla, by marketing the MachE as a mainstream EV Ford will likely end up facing many of the same issues with lower range models.
