> that it is actually up to date (and if it's not, you generally have to wait 6+ months for the next version of the distro to roll out, and then you upgrade EVERYTHING to get one package updated).
That is true and certainly very bad. But it doesn't need the "windows way" to get fixed. Providing newer versions of selected apps with repository model without full upgrade of distro is possible, as done in debian-volatile. However, it requires that the application developer is careful enough not constantly move to using new features of underlying OS libraries.
> The Windows way is far, far, far more user and developer friendly. Users don't find software by browsing a freaking package repo.
Not true. Don't think windows, think Apple. iPhone App store specifically. Not on desktops yet (apart from steam), but the "browse package repo" model is very much there, easier to use, and I have no doubt it will come to Desktops eventually.
Why is it more easier to use? when googling, you get links to lots of stuff that a) isn't application b) isn't application for your system. In a app store every search result is a application for your system. App store also puts a limit on malware and crapware if there is some QA control, user feedback loop and recall feature included. The repository model provides fixes and updates of installed applications automatically. In windows model most apps get never upgraded after installed, while other applications create their own updaters.
The only use experience difference (lets ignore that app store bans GPL and ubuntu propiertary software for the sake of discussing just UX) between app store and say ubuntu software central is that developers contribute directly to app store while in ubuntu it is typically done by ubuntu developers. Now of course the upstream can contribute directly to ubuntu, and some do. However, they really don't make it clear and certainly make it a hassle to do so.
> The Windows way is better for developers because it gives them the ability to create ready-to-go installers instead of having to wait for half a dozen popular distributions (and hundreds more of unpopular ones) to actually package up the software
Now this is the real problem. However, windows model won't fix it. Instead of making packages for dozens of distros, they would need to make their installer support dozens of distros. Not a big win.
The only solution is to make most distros die. Kill one linux distribution by implementing its added value in a mainstream distro and we are one step towards global domination. Unlikely to happen, distro developers are too emotionally attached to their own distributions to let go.
However, the time is on our side. More and more software needs not be installed at all. How many of your non-tech friends install local email client instead of reading gmail in a browser? Instead of installing inkscape why not point your browser to http://muro.deviantart.com/ ? Tax software, why on earth would something that needs essentially forms and buttons be a installable binary that needs regular updates? With WebGL a good deal of games can be implemented within browser. And other emerging html5 features continue to push more applications to the browser.