Admitting Where it Sucks
Like anything, in order for Linux to improve, especially on the desktop, I think we need to look at the areas where it NEEDS to grow in order to be better, not just everything random that's "wrong" with it.
On the desktop, Firefox is well on it's way to rivaling and even beating IE. This is especially true on windows. On Linux, it's flagging for two main reasons.
1) Fonts
I know this has been beaten to death, and you can control the font size within mozilla, but for the life of me, I can't understand why you can't change the "proportional" font. It's The main, default font that firefox uses, and all you can select is "Serif" (aka times) or "Sans-Serif" (aka arial).
The BitStream fonts are awesome, especially on my LCD screen with sub-pixel hinting and anti-aliasing turned on, but if I can't choose them for the default, it doesn't make a lick of difference.
My own sites included, any given site utilizes some rather small fonts without specifically defining a strict font family, and the default font that gets picked by Mozilla is a jaggie covered mess at 8 pixels.
2) Plugins
I know this is the fault of the vendors, and both Real and Macromedia are getting behind Linux "Real Soon Now," but this is one of the most annoying and troublesome things for the casual "Linux on the Desktop" user. For me, this isn't that big a deal. With the exception of being really miffed that I can't check out homestarrunner.com from home, I really couldn't care that much about watching DRM riddled formats right inside my browser. If it can't save it to disk and watch it from there, it doesn't deserve my eyeballs anyway.
Sara and anyone who visits are another story. It sucks some serious butt to have friends come over and go "Let me show you this" only to have them sit down, get to the site, and then have it COMPLETELY not work. This has happened multiple times recently with Flash, Real, Quicktime, and Mpegs.
I know, each of these issues (with the exception of advanced or new-ish flash) can be resolved by installing the correct binary plugin in, or working such and such kung-fu, but i don't have time to do that when they're sitting in the chair and it just isn't working. To Paraphrase Eric Raymond's recent triade, If this was aunt Tillie's home desktop, this just wouldn't fly.
Many will say that if it's broken, why don't I write the fix. My answer to that is simple. I don't wanna, and neither do other open source developers. I don't have the time or energy to write a support plug in for a format that can and will make a company money. It's time for these companies to realize that if they are going to push their plugin architecture as a de-facto standard, Windows and Mac aren't the only game in town. Linux just quietly surpassed Mac OSX in desktop market share, yet it only gets about 1% of OSX's play because it doesn't have a major advertising force behind it.
Yet.
The next 3 years should be interesting. Linux on the desktop has hit a few major roadbumps, with browser plugins and licensing squabbles (XFree86, apache) among them. My prediction? Vendors will begin to open source their drivers and plugins, realizing that their precious trade secrets are secrets at all, the secret is that they beat their competitor to market with it, and did it better. Anyone with a decent developer or 2 and some cash to pay them could have reverse engineered the driver by now, so crack it open, and make it usable everywhere!
3 Years from now, we'll be saying "Remember when drivers were binary only sometimes?"

