I want to thank everyone who took the time to answer me! WOW!
So yesterday I went to at&t to grovel about upgrading a bit early and getting the HTC inspire. Well when I told the at&t guy why I was considering switching (my constant issues with iTunes, sync issues and that I just feel itunes needs too much attention) he talked me out of switching! The at&t guy said Android requires way more attention then an Apple device and does not flow as seamlessly as iTunes/Apple.
I dont know that I believe him

I do know that I called iTunes yesterday afternoon and calmly explained every single issue I have had with the phone/iTunes/syncing and they helped me go in to straighten some things out... for now. But what usually happens is everything works as it should until the next software upgrade, then I will go to sync my phone and all my crap will be gone again. iTunes will not be able to locate the files (which are in the exact same place they were in an hour before) and therefore I will have to fix it again...and godforbid we dont back something to external hard drive.
What to do, what to do? lol
Thanks so much for the feedback. Much appreciated everyone