How to sync more than one of our iPhones to my iTunes account?

Does anyone know how I can go about syncing my husband's, or my two teens' iPhones to my iTunes account on my iMac so we can share applications I've purchased? I think we're supposed to be able to do that aren't we? I thought up to five computers or five mobile devices on one network (our wireless network) could all sync to one iTunes account? But we aren't able to figure out how.
So far we've paid for Super Monkey Ball twice now because my teen convinced me that I just had to purchase it in my iTunes account, then he'd be able to hook up his iPhone to my computer and get it from me. But that didn't work. So I ended up with a ten dollar app I didn't want, and he had to go to his iTunes account on his computer and buy it again for himself. Now I have many apps I've purchased but would like to share with my family. If I'm wrong and we can't share, then so be it, but I just want to be sure. I've heard more than once recently that we're supposed to be able to share somehow, and not just apps, but most anything we have in iTunes, maybe with a few exceptions.
Thanks in advance!

Not sure why I haven't gotten any replies? Is the question just stupid, or is it that no one knows the answer? I truly have tried to find out the answer to this question, but everything I've found has been very confusing. Please someone help us figure this out!
Thank you, Deb

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