Transfering Purchases To Itunes - Any Way to Recover Purchased Songs/Apps?

I. Am. So. Angry.
This is why I hate itunes!!!! Everything is so confusing!!! Someone, please help?
I have Itunes v10, and an updated Ipod. But nearly every time I transfer purchases to my computer, it doesn't transfer something, yet no error comes up to warn me! And then I sync my Ipod, thinking everythings good, and all the purchased apps and such will still be there... BUT THEY ARE MISSING. I did not delete them! And they are gone! WHYYYYYYY
This has happened with countless apps and music files. Is there any way to recover purchased things? I DO NOT WANT TO BUY THEM AGAIN.
OK.... Calm down, Uo.... sigh
I have divorced parents, so I have to sync my Ipod with both computers... I have not found out how to do this. Can someone explain how? I think homesharing might work. Also, I want to be able to recover my lost PURCHASED apps/songs. I am very displeased and may never buy another itunes card or product. Every. That's how upset this is making me. PLEASE HELP. And explain in detail, I am stupid.

OH MY GOD.
Itunes, I take it all back. You are the best. I don't care if you will take over the world someday. You are amazing. As long as I can get my apps again, for free, I love you and will never complain.
I just went to buy it again (sourly) and clicked purchase, but then it said I already bought it, and to clikc 'ok' to download it for free! I LOVE YOU. I LOVE THE WORLD. THANK YOU!!!! ♥♥♥
-Happy, and now promising to buy more itunes cards, Uoneko

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