This is a huge topic really, but one that I cant resist to throw my ideas into. I think most people who might be interested in switching to GNU/Linux are in exactly your possition. You wonder if things will work, if there are applications available to do what you want, and exactly how difficult is GNU/Linux to use.
To answer a few of your questions.
- As ive said in previous simular threads. This really depends how far into it you want to go. If you have the time and patience, I would always recommend Gentoo. Its very hands on, and just building the operating system (yeah, thats right, its pretty much all built from source) will teach you allot about how GNU/Linux works. It will also teach you where all the different configuration files are kep, and exactly what they are used for. Gentoo also has some of the best docs, and a massive, very helpfull community. Hell, if anyone from here wanted to install Gentoo, I would personally volounteer to hold your hand all the way through the install.
Other distros (Fedora for example) wrap up most of this sort of stuff (hands on stuff) into guis and other tools, so you dont really see whats going on.
Basicaly, if you want to learn GNU/Linux, Gentoo is great. If you want to just use it, get comfortable and then maybe go for a more advanced system, something like Fedora would probably be a better chioce.
To be honest, I started with Fedora, but because of all the gui tools, got bored with it pretty quickly. Ive been using Gentoo now for about 18 months.
Not that difficult at all. There is an alternative Linux application to every windows application, and most of the time there is more than one chioce.
Sorry, NTFS are still read only as far as I can tell.
As I said before, there are alternative apps for everything. You can even use your iPod.
The linux shell is a whole environment in itself. There are several shells to choice from, the default being bash. Bash is a general purpose scripting language that is failry easy to learn. You can access any linux commands from within this shell environment, and as someone else pointed out, they are all (most of) pretty well commented. If you install bash-completion, you dont even need to remember all the command names, bash will help you find them. On top of all this, you can create your own aliases to common commands, functions, and entire scripts to run as commands.
Of course you can dual boot. You'll need to install windows first though as it f**ks around with the boot sectors on harddrives.
Ive probably gone into a little too much detail here, but really, Im just trying to get the point accross. Once youve used GNU/Linux you wont go back to windows. Its so much more productive, customisable, educational and fun to use.