i made some serious progress here.
first, by a combination of google voice, sipgate and sipsorcery i am now able to make unlimited free calls in and out of my borrowed iphone, 100% over wifi (it doesnt have a sim card)
skype didnt have what i needed. so it got tossed out.
the best app (By FAR!) that i found was a free app called meebo.
if you jailbreak your phone and get an app called vlc4iphone you can play flac's with it. however.. due to quality and glitchy-ness ive lost all interest in using it as a music device.
does it work with linux? not really. i had to use windows to jailbreak it. and so i just used windows to copy over my google contacts as well.
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conclusion. it works. but not super well and i think its just the OS. even with the added functionality of jailbreaking and using "backgrounder" it wasnt even close to 100% usable. i constantly had to reconnect things. so its cool, i like it. but i dont think im going to buy an iphone or ipod in order to get what i want. im going to keep looking at other similar (but hopefully better) devices.
by the way. DragonSearch has absolutely nothing in common with google voice. i think you might be just a tad confused about what google voice is, and does. but thank you for the reply.