Confusion on the whole iTunes to iPod transfer

Several issues: 1) after buying songs in iTunes, I can't figure out how to get them on to my iPod (video and shuffle) without deleting the songs already there. 2) I got the new songs on to my video iPod and then my library in iTunes don't show all my previous purchases?? 3) I find the website to not be user-friendly for steps to easily continue purchasing songs and adding them to my ipods?? Help?? I'm usually pretty computer literate and this website I find to be difficult

Do you have you ipod set to automatically update or manual update?
Do you have the latest version of iTunes 6.0.4 (3) ?
Do you have all your tunes stored in iTunes in your computer?
(If you have the ipod set to manual update you can just drag and drop and it won't erase other songs!)
I had an issue previously with songs not uploading because I didn't have the appropriate iTunes updated software.

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