The only thing permanent is change.
I started using Cakewalk almost 20 years ago, when I picked up a copy of Professional 6, back in the Cakewalk Pro Audio days. Running Windows 95 on a PC.
Back then the community was mostly MIDI users, with the option to record some audio. But chances are your PC wasn't really up to much digital audio, and real-time monitoring and effects were almost impossible. Record dry and add off-line effects after. I remember most pro audio newsgroups on the net were still discussing analog tape and the new ADAT format.
But Cakewalk eventually sucked in enough of the pro audio crowd to keep rolling. PC technology took off, and it wasn't just tape machines or Macs anymore. Lot's of those guys in the Cakewalk forums these days.
Then they marketed to guitar players. There's a lot more of them around here now than pure MIDI users. There's more guitar players on the planet than anything else, I presume. Guitar Rig and TH3. Lot's of those guys in the Cakewalk forums these days. Not a problem! Some of my best friends are guitar players
But in the middle of all this, they didn't forget about the MIDI guys. Lots of cool virtual instruments are bundled now. Hardly ever need to break out the external hardware anymore. Plus I really like how you can now record a virtual instrument directly to an audio track, completely in the box!
The younger crowd now appears to be into electronic dance music and making beats. So the marketing goes there. Loops, anyone? Improvements to Matrix view. New Lens just for making beats. Lot's of those guys in the Cakewalk forums these days.
I think that the way forward will be to successfully appeal to all groups of users. From posts that I have seen recently, the most neglected groups at this time apparently are traditional songwriters, composers, and arrangers. They either just make do with Cakewalk, or use another product that does what they need.
The bakery can focus attention on the most wanted new features. Then the bakers obviously will have to balance their resources with what they can market, and how to keep bringing in new users.