Daily updates give you the best software and security immediately,
It can also possibly introduce bugs with each update. And I totally disagree about 'the best software'. For 3rd party developers, the OS updating daily must be like chasing a moving target. Who's to say tomorrow's OS update doesn't break something or cause instability in todays application update? There may be some advantages to such frequent updates, but I wouldn't argue that better software was one of them.
Also, I'm curious, what happens if you leave a system off for a few weeks (or pick any length of time) and then come back to update it, having missed however many daily updates? Is there a logical rollup of previous critical updates and possible broken dependency issues, or can you just start updating from the latest daily without it mattering how many you missed?
Windows and OSX don't upgrade core features.
OSX certainly updates core features, just with logical 10.x.x point updates.
You get security patches, and occasionally some minor features.
Which is all that's needed.
To do a rolling release with them would require a subscription.
That's not exactly a selling point for rolling releases then.
You spend two minutes a day updating your systems- I spend zero minutes a day updating my systems. Bottom line: if things work and are stable, then that's all that matters.
Problem #1: The assumption that Agile forces bad updates. Total nonsense.
I'd much rather see small, incremental updates every 3-4 months than one giant service pack every 1-2 years that introduces so many bugs that the first month post release is miserable until they release 10-20 patches to fix the fixes.
The incremental update process you're describing is exactly how point updates work.
Windows service packs (and Mac Combo updates) are really just a roll-up of previous updates, not a whole collection of new untested updates. I don't recall any MS service pack (or Mac Combo update) that was a PITA for a month before being patched constantly like you describe. Or was there a specific such update you're referring to?