Wireless and Linux
I can get hermes, orinoco, prism, atheros and centrino (ipw220) chipsets working out of the box with any Linux that supports the Gnome Network manager (which I have installed on Ubuntu 6.06 - it's in the repository). I can get the ralink and derrived chipsets working for WEP without too much trouble, but it takes some effort to get WPA working, which most people will not be able to sort out themselves.
Where there is a weakness is in the WPA supplicant support. Atheros and Centrino chipsets with Gnome Network manager will do it, and in a reasonably friendly way.
I am using a fairly backward Ubuntu release, so I suspect that it will be a little easier in later releases. I know that the normal network system admin tool in the menu does not work with WPA at all in Ubuntu 6.06.
Where the problem lies is that with a card intended for Windows, the user gets the nice little install CD, which takes away from them all the hassle of deciding which chipset is being used.
Modern Linux distributions probably have the abillity to drive almost all of the chipsets used out-of-the-box, and also have the NDIS wrappers as a fallback, but you need to be able to decide which chipset is in use to make useful decisions.
If manufacturers provided the details of the internal workings of the card (basically the chipset details), or even gave the same degree of care to installing their products on different Linux distros, as they do on different Windows releases, then I'm sure that there would be less discontent amongst non-hardcore Linux users.
I know that this is hampered by the plethora of different distributions out there (see my earlier comments), but it should not be rocket science.
An additional complication is that if you go into your local PC World (assuming it is still open after Thursday) and ask for a Wireless PC-Card using the Atheros chipset, you will get a blank look from the assistants, as they will understand "Wireless" and may understand "PC-Card" (but you might have to call it a PCMCIA card), but Atheros might as well be a word in Greek (actually, it probably is).
And it complicated by manufacturers who have multiple different products, with the same product ID, using completly different chipsets (if you are lucky, on the card itself, you may get a v2 or v3 added to the product ID, but not normally on the outside of the box).
If you definitly want to get wireless working, I suggest that you pick up one of the Linux magazines (-Format or -User) and look for adverts from suppliers who will guarantee to supply a card that will work with Linux, or keep to the Intel Centrino wireless chipset that fortunatly is in most laptops with Pentium processors.
If your laptop uses mini-PCI cards (under a cover normally on the bottom of the laptop) for wireless expansion, then there are many people selling Intel wireless cards on eBay for IBM Thinkpads (2915ABG) that will probably work. Thats what I am using, and it works very nicely indeed.