Soundwise 
I wish Cakewalk had a more predictable cycle, like
1st month dedicated to audio related new features and enhancements
2nd month - MIDI related new features and enhancements
3rd month - UI optimizations.
Listed in no particular order but this could help with keeping priorities even.

Someone from Cakewalk can chime in to confirm or deny, but I think that would be much more difficult to implement because it would tie updates to a rigid schedule, which is currently not the case and schedule rigidity seems to be what concerns people ("they have to come up with something every month").
 
In the present system, Cakewalk is always working on various things in parallel, so it's difficult to predict when some features that are in progress can be "harvested." A monthly schedule isn't really that onerous because there will always be something that's ready. But if you specify that some specific element has to be ready by a specific date, then it gets complicated.
 
Here's one example based on content. I created several multiband track templates for a prior release before Patch Points existed, so they were fairly complex and involved buses and audio tracks. At that time, Patch Points were scheduled to come out at some point and they would create a much more elegant environment for multiband, so CW held off on the templates...fair enough. Then Patch Points appeared (I believe ahead of schedule, but I'm not sure) so I redesigned the templates to take advantage of Patch Points.
 
However, at the last minute QC found a strange bug where the multiband track templates didn't reference the patch points but hardware inputs if they were the very first, and only, things inserted in a completely blank project. So, the track templates didn't make it into that release either. Then they found the bug, fixed it, and now the Track Templates are good to go...hopefully  
 
I use this as an example of Stuff Happens. Things that were expected to take longer sometimes don't (like some of the optimizations) and things that are expected to happen sooner don't (like the Drum Replacer). But because of the flexibility of the current schedule, the optimizations and Drum Replacer showed up when they were ready.
 
Again, someone from CW can chime in but I get the impression that as long as the requirement is something every month, that's fairly easy. If the requirement is specific things in specific months, then it gets difficult.