As far as linux goes, I'm a Debian guy. I don't mind poring over obscure text configuration files and doing all of my package management at the command line. That being said, I was intrigued by all of the articles I have seen lately (such as this column by John Dvorak) about how easy Ubuntu is to use and how it's ready for the desktop.
A few weeks ago, I decided to try out Ubuntu 9.04 (Jaunty Jackalope) -- actually, I'm trying out Xubuntu 9.04 (the version with the XFCE desktop environment). I gave it a shot, but I have to say that I'm disappointed.
Of course, the average person will probably never be able to install linux (just as the average person cannot install Windows from scratch, either). But there are some basic things that a user should be able to handle through the GUI by now. A few years ago, the big problem was with wifi -- how can you really expect someone to compile a custom kernel just to use wifi? Now that they've sorted that out, the major problems are smaller, but just as major.
I have a small FAT32 partition at the beginning of the drive for WinXP. I had the partitioner leave this unchanged, but it rendered WinXP unbootable afterward. I haven't tried the equivalent version of Debian, so I'm not sure where the problem lies.
Ubuntu has a really beautiful GUI for changing configuration settings. There's a nice Windows-like menu for changing resolutions, for instance. Which is great, except that it keeps defaulting to a resolution that doesn't display properly every time I reboot. Why doesn't it save the screen resolution setting? I ended up adding an xrandr line to my ~/.xprofile.
Synaptic is a really nice-looking package management system. You get a list of all of the available packages, making it very easy to find packages to install (or remove). The problem with Synaptic is that every time I fire it up, I have to wait for a while for it to build the list of available packages. Why can't this search be done in the background (so that there is no wait when firing up Synaptic)?
By default, X.org blanks the screen after a certain period of inactivity. Why is it so difficult to disable screen blanking? I had to try 4 or 5 different xorg.conf hacks before finding one that actually worked.
No doubt Ubuntu has come a long way, but it's still got a way to go.
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