Sort of a catch22 for me. I find myself being able to test almost every feature now as it is released. Because of the fact that there is only one or two at a time for me to digest, I probably spend more time testing features than I used to, and less time creating music. Or perhaps more time in general at the computer.
However, now that I'm better acquainted with the features, I find I can do things quicker, and with more confidence that I'm using said features to the best of my ability.
I too feel that I'm rolling the dice with every upgrade, and cross fingers, toes and anything else every time I update. I do, however, update my laptop first and check to see if there are any major downsides before I update the main computer, and I feel this helps make the process easier.
Overall, I feel ok about the way updates are gradually implemented, and so far have confidence in the update process.
The one and only time I had a glitch with an update, with the help of forum members here, and Cakewalk support, I was able to find a solution to the issue and be on my way.
This leads me to the fact that one of the better things about cakewalk is their level of support and the friendliness/helpfulness of the Cakewalk users.

I do not see how any intelligent human being can honestly argue with the current system... You don't like to update monthly??? Don't!!!  You worry about bugs???  Wait awhile... You want something new?  Lobby for it in the Suggestions forum and you might see it in a month or two...You wanna get things immediately??? Download and deal...You too overwhelmed with all the things you can do that are new??? REALLY??? Friggin' unbelievable, especially when you can ignore them.
 
You don't like the DAW??? Go away...
 
whiners gonna whine no matter what the bakers do...Indeed, whiners are on all DAW forums...I've perused them all, and they're all the same...  whining seems to be the state of a certain segment of our species these days.  Flamers and whiners... 
 
I'm on the side of flexibility, rapid response, constant error checking, and the excitement of anticipating and the amazement of the unexpected.  I spend as much time as I desire on keeping track of and trying out new features; many, like the much lauded drum replacer I've totally ignored...Someday I may think back and say, "wtf were you thinking... this is amazing!~!!!!!" but I just don't care at the moment...and I am happy for all those who find this truly amazing.   Now the midi/audio recording... WOW!!! I've been all over that... totally changed things for me in setting things up and playing around...Aux tracks??? I'll get to it...
 
I think the Bakers new innovative recipe for brewing and introducing new "flavors" tastes scrumptious and they have my gratitude...

I just update when I see a feature that I "must have" or if there is a bug fix I really need.  This equates to updating every few months and as a result, I am not overwhelmed at all.  The choice is always yours to make, so there is really no need to follow the monthly update schedule if you would rather sit stable for months at a time.
 
Much has been made of the hassle of having to update.  I am at a complete loss to understand that, because most of the time, the only reason to update is to get something new you need/want.  If you choose not to update, you are effectively on the old model - problem solved.
 
If too much choice or too many updates are the only thing people have to moan about, we must be in very good shape.

I will surely renew my membership in January . . . not because of such shiny new features like Mix Recall, Drum Replacer, Vocal Sync, Windows 10 compatibility, VST upsampling on playback, onscreen keyboard controller, new start screen, Mastering FX chains, Project Templates, numerous content offerings (sorry Craig) . . .
 
 . . . but because of all the core enhancements to the Cakewalk software like ARA,  Midi engine improvements, virtual instrument streaming improvements, audio engine improvements, CPU power savings, PRV and Staff view improvements, new Control Bar, Sonar Forum upgrade, Prochannel FX rack, Recycling plugin windows, Audio Export/ Import improvements, improvements in VST third-party compatibility, Direct synth recording, Patch points. . .
. . . these are where the real cake is . . . everything else is just  . . . well, too much sugar for me, things I haven't found a use for in my workflow.
 
Always wondering what's coming out of the oven next with these monthly updates, but clearly there are lot of things Cakewalk are doing that I don't need, though I have much admiration for what they have done in terms of stability and general usability, that I really enjoy supporting them always moving ahead with the product. 

As I said, I'm simply going to update less frequently because it is more comfortable that way for my workflow. With the old system, I could leave X2 in place while running/testing X3. If they found a way to do that it'd solve all my "issues". Which really aren't issues at all, I just replied to the question "are you overwhelmed by the frequent updates". Maybe "overwhelmed" is a bit strong but I've been remodeling my home and for a while it seemed like every time I got to sit at my DAW there was a new update, even though I hadn't even really been able to check out the older one.

I generally install each version as its released. There was one where I delayed until I had researched all the complaints. As often is the case, the complaints seem to fall into the categories of user error, system specific or not show stoppers.

I have confidence in the release program that Cakewalk has in place and I'm comforted by the rollback feature. Really, an installation and rollback takes literally minutes only, so there's no drama. The biggest advantage I have is that I'm not the paranoid type who expects there to be a problem.

Personally, I've never felt overwhelmed with the monthly update system as I regard innovation as a major plus point, especially as new features are commonly accompanied by core program improvements.

I guess I'm used to the idea, as my other 'couldn't do without' software (Unity3D)  is updated regularly via a 1.6GB download. These updates often include significant scripting changes, requiring the user to recompile existing projects or make manual amendments to custom classes.

I don't view these updates as a problem as I always end up with an improved creative platform. In fact, I look forward to them :-)
 

I don't use many of the updates so I just ignore them.

I am overwhelmed by how good the damned subscription is!

Best value in the business, warts and all, because nothing is perfect and there is room for improvement. Keep them coming!

Very interesting, often solutions and features can breed problems and difficulties.  Since 99% of my work is client based, I am far less likely to upgrade my production systems since I typically have 5 to 7 client projects in motion at a time.  Therefore I upgrade on my test system and work through all of the things described above without the risk of my projects or precious time being lost.  My production system gets the upgrade when it makes sense.  I don't focus on a time window for upgrading the production system, it is based on client project deadlines.  Since 2003 the least number of simultaneous client projects I have been working on is 3 - for some of you, remove the word client and just think 'important' projects. So based on the delivery dates and key post production schedules of those projects, my production workstation will get stable and well tested upgrades. 
 
We could all go VM with test and production.  I suspect in development that's what the dev team is doing.  I think about that environment every year.
 
-D