All these issues have very simple ways to resolve them...
1) iDump is a pretty good way to move your music on your iPod to your computer. Free and fast, too.
2) I have an iHome and I can use every gen iPod made so far with it. It came with different size docks so it's adjustable to fit different sizes of iPods and it works damn well. If yours doesn't work that well, that's not Apple's fault. They've created a $2 billion accessory industry for the iPod, not exactly a monopoly.
4) The .m4a file was an audio format made specifically for the video iPod so that it could sync with video feed more efficiently. If you really hate it you can a) convert the files yourself or b) use a different program to rip music onto the iPod. I must also remind you that .wma files are designed specifically for Windows applications, and Microsoft makes a significant amount of money selling licenses to music player manufacturers. It doesn't take much reason to figure out why Apple wouldn't shell out money to Microsoft for a license they don't need. The real question is why Windows Media Player doesn't have a built-in converter to switch .m4a files back to .wma yet.

Personally I have enough experience with other mp3 players to realize that the vast majority of them are complete shit and not worth the money spent.

DO you know if there is any way to use Windows Media PLayer to do this?

Thanks for the advice. I just put my library into Media Monkey and am now syncing Ipod with it. Great program. I even have a WMP11 skin to go with it.

I will try this. If it works like you say thats great because I really need a place to back up the music. (Portability as least)

It looks like other people addressed you other points, but I just wanted to mention that WmA is not the format most CDs are in. In fact I've never seen a commercially produced music CD that was in that format. They are in a format that is native only to CD players, so anytime you are importing songs from a CD to your computer you are converting them to something whether that format is WmA or m4a or mp3 or wav or whatever.

Also, iTunes does play some Window files, such as wav.

Ic. Every CD I have gotten from the library and burned to my computer through Itunes would say that it would have to convert it from .WMA to .m4a

CDs use a format called Red Book audio, your computer displays it as .WMA because Windows has to translate it to that format to make it readable. I'm on a Mac and when I put a CD in my computer I never see .WMA and instead see .AIFF (or I think sometimes .WAV) because that's how my computer translates it. The extension you see is based on what your particular operating system uses rather than what the CD itself contains.

Anyway, why would you have to convert it to .m4a? You can set your iTunes preferences to import it as a whole bunch of different file formats.

I just wish Macs themselves weren't so goddamn expensive.

Allright that makes sence then.

And it really doesnt matter now, ( would have been nice to know though) I just switched over to MediaMonkey and am very pleased. Syncs well, many great features and some solid skins.

True that. I always get them because I do freelance work and they're the standard in the industry I work in, but I sure wish they were cheaper.

Funny thing is, this person created the exact topic on another forum I go to. 4 minutes before this one :D