There are clear hints on how to avoid large-scale disasters, e. g. public beta programs and slow roll outs (where only a small minority of users are initially updated). The fact that you separate software and the cloud makes me thing that you haven't noticed where Adobe is going: there is a cloud component to their software ecosystem (e. g. my gf has a portfolio on the Adobe cloud or Lightroom syncs via the cloud with the iPad). Many pieces of software not only tightly integrate with the cloud, but the cloud becomes an indispensable part of the software itself.
Of course there is a Cloud component to the desktop software and one of my main complaints about CC is actually the LACK of really compelling Cloud services being offered. Things like the auto saving of project files to the Cloud and profile synching are nifty but not really show stopping. The Cloud storage and synching of files is kinda a dime a dozen these days and Behance isn't exactly a household name.
I'd love to see something like distributed computing helping on big renders or access to a quality (and growing) library of stock footage, photos, effects seamlessly from inside Adobe's apps (I'm hoping Adobe's recent purchase of a stock footage company is a step in this direction). MediaSilo and Adobe have announced an interesting partnership, but you have to pay for a MediaSilo subscription too so it's not part of CC.
Does this desire for more Cloud services mean, for example, that I want PPro as a Cloud app like Google Docs? No, certainly not, but I do want to have Cloud services from Adobe that enhance the abilities of the PPro that's running on my local computer.
Painless updates are a reality on iOS, and in part they are a reality with OS X (with a few more caveats, of course). It's not a question of »if« but »when«.
Really? Wasn't iOS 8 kinda buggy, so they released 8.0.1 but that was even worse, so they pulled 8.0.1 and got 8.0.2 out the door ASAP? And users running Resolve on new Mac Pros are still having show stopping GPU issues (users running Resolve on Windows via boot camp on the same machines are reporting no such GPU issues). At least Apple managed to fix the 10.9.x issue that caused Adobe apps to malfunction if they were set to use the GPU.
My favorite is probably from a number of years ago when an update to iTunes prevented users from exporting from After Effects (it was a DRM update and made QT think that AE users were trying to create illegal movie files). With all the permutations of hardware and software it's impossible for a company to say with 100% certainty than an update won't cause any problems so I don't care how kinda better it's gotten, users should always have to the power to control when (if at all) updates are applied to their computers and devices.
On 10.10
security updates are installed automatically by default. It's a matter of time when all updates are applied by default, although that may still be a few years off. Apple transitions slowly and deliberately.
Right, like I said, it's a separate check box. The user still has option to uncheck the box and manually control updates. With Google Docs, for example, there user has no option. Google usually tries to transition slowly (many times giving people time to stick with the old version for a bit before until it disappears forever) but the user has no control over changes to the software.