You rarely ever DO hear the greatest players on the latest technology. Most of them are probably all too aware that any time spent trying to learn the OS and workflow of whatever is 'latest and greatest' is time they can't spend PLAYING (or practicing!)....
Unlike so many here, once they find something that suits them, they will skip several generations of new models, until something comes out that is SO spectacularly better (at what they need!) that they MUST have it. But incremental improvements don't cut it.
One thing to bear in mind is that, the vast majority of 'great' players refuse to use any auto backing whatsoever (no shortage of great players willing to play with them!). All they need in a keyboard is that it makes their favorite sounds, and that's it. No need for updated Songbook 'features', no need for a better OTS implementation. Just the sounds, ma'am...
For all of you out there that DO update and change arrangers and keyboards on a regular basis (more than one a year), just ask yourself this... If you spent EVERY hour that you have spent on transferring and tweaking SMFs, editing styles, updating Songbooks, and learning new or changed features on actually PRACTICING... scales, songs, solo techniques, do you think you would sound better on your current arranger WITHOUT the practice, or would you sound better on your old arranger after many, many hours' practice?
Me, I'm inclined to think the latter...
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An arranger is just a tool. What matters is what you build with it..!