some people pick linux up quick, some just dont' get it. the more you know about "how" a computer works, the easier it is to overcome the differences between windows and linux.
seems like everybody knows linux these days, so i doubt you have a huge learning curve. i've been using linux for over 10 years, and it has changed alot. you don't have to know as much to install/use linux anymore.
short answer, try it. download an iso for some bootable disto (slackware/dsl/dynebolic) or grab some redhat disks and follow the prompts.
the biggest drawback for linux is good GPS navigation software. however, linux handles media playback fine. if you're into it, linux also makes it alot easier to "understand" the wireless networking environment you live in. *grin*
as far as benefits, it's great for diskless environments. you can boot from CF or USB directly to ramdisk negating the need for a hard drive in your carpc.
i havn't looked into windows ability to do this, but i would assume it's a no-go.