I can feel for those that want a "secured" place where they can work without bumping into a new learning challenge. Been pressed to learn new things can disrupt the working flow, and slow down your production.
For myself, however, things are always "on the move". Music is not the only "discipline" I am working in. I also work with graphical art, especially with holographic 3D constructs (yes, I own an holographic vibrant-isolated workbench and a couple of lasers) and 3D printing. I own several DAW's (Ableton Live, FL-Studio, Cubase and Sonar) and use them not only for myself, but also for those that need some recording and (a bit of) mastering.
Needless to say my learning process is never "finished". I am always on the move, learning new techniques and looking out for new developments. It can be a bit overwhelming at times, and I am not getting any younger (I am 62 now), but I love to delve into new things and keep learning whatever I can.
As said, I can feel for those that feel forced to "jump ship" and feel pressed to learn a new DAW, but I do not think it is very handy to "lay all your eggs in one basket". For AdamGrossmanLG I would advise to alway have some knowledge for at least two DAW's. If something like Sonar happens to your new DAW, you always have a "backup plan". It is always a good idea to figure out how you can move projects from one DAW to another. I should advise to do that at least one time with a medium large project as "learning experience". Knowing how that must be done will make you feel more secure in case of calamities.