> Tiled windows are a waste of screen space; I have far more open windows than can ever fit tiled.
That's what multiple workspaces are for. Tiling WMs are especially great when working with large and/or multiple monitors. You're not forced to always use tile mode, you can easily switch between layouts via hotkey: http://xmonad.org/tour.html
Also, a lot of smart people disagree with you: https://news.ycombinator.com/item?id=3964530
> <Package management>
You don't want to update for fear of breaking something, yet you admit your problems stem from never updating.
Have you thought about Debian Stable/Ubuntu LTS releases?
Are you really complaining that Debian/Ubuntu package availability? Even if the main servers disappeared, you're ignoring the fact that there's plenty of mirrors. What happens if microsoft.com disappeared?
> <file browser density>
Hit Ctrl -: http://i.imgur.com/0xWSw.png
Explorer looks less dense, doesn't have tabs, split panes, copy queuing, real file modification tracking (Explorer requires F5 to see changes). It doesn't auto-adjust column widths, look at file size as an example. Not to mention the explorer.exe process doubles as the WM, so when it crashes all windows get reset.
Nautilus has a better hotkeys. Alt + Home to jump back to home directory, F9 to see symlinks to common directories, Ctrl + H to toggle hidden files, Ctrl + 1/2/3 to change views.
You could have not chosen a worse program to compare between the two OSes.
> <driver issues>
That's a result of market dominance, not anything intrinsically different between Windows and Linux. Congrats!
Have you tried installing a clean version Windows 7 on a laptop? Have you noticed how many proprietary drivers you have to download and install? I did this a few months ago with a new X220 and spent 4 hours finding, downloading, and installing drivers. If Lenovo.com disappeared, I'd be SOL.
Take any laptop and clean install Ubuntu and Windows without internet access. You will have a better working system with Ubuntu.
Due to lack of proprietary drivers, Linux actually has much better support for older hardware. Not to mention a large source of Windows BSODs are due to low quality, 3rd party drivers running in the kernel.