That's because switching to another working environment requires lots of mental energy - you have to evaluate gains and loses first(eg if switching to a particular DAW worth it to change your habits and to abandon already burnt into brain knowledge of your present DAW). For a pro it's a very time and energy consuming process - you literally have to make lists of things you do in a program and how you do them; then you have to try it in considerable option(s). Then you can get approximate evaluation of potentially new workflow and make at least half of the decision(will you drop the idea of switching to this DAW; will you keep working on your present DAW, but use the new one from time to time until you can make a final decision; you're convinced and ready to switch). After this you'll face one problem(even if you decided to switch now) - certain instruments and techniques you used in previous daw and how to get them in a new one - can you replace it with the new toolset or maybe some of those I's and T's not that important and you can achieve the same or better results with provided toolset instead of trying to replicate what you were doing so far in the previous host. And finally you'll have to repeat the process of burning control of the daw into your brain(which includes reading manual, watching since videos, trying things out, learning/assinging hot keys and so on).I know pros in LA who still use ProTools and hate every second of it, but still use it because... everybody is using it. Some PT diehards can't take it anymore and are switching to Logic. When I show them what Studio One can do, they are shocked/baffled/amazed but still won't switch because... well... because...
I described this switching event in a very-very broad and generalized way, but you can see that this is a complex process. This is very rare when people over 50 are willing to get through all of that again. If should be something revolutionary to make the switch a no-brainer. This is one of the reasons why we shouldn't focus on the "old squad"(no offense, besides we all gonna be there sooner or later)..
Finally, everyone I know, who switched to S1, put the main emphasize on streamline workflow of S1. That was the reason I switched, too. I myself think that gains in comfort and speed is much more than that time I spent on all the mentioned activities.