Setting up Brand New iPad 2 - iTunes Sharing and Getting Files from old iTunes Account

Greetings. I recently purchased an iPad 2 (convert after 20 years of PC use) and have been waiting to set it up until I knew the proper way to proceed. I have multiple questions and am hoping those of you with more Apple experience can help out a convert .
I would like to set it up with a new iTunes account so when my wife gets her iPad 2 next year we can share apps and movies we buy on iTunes. Do you always have to sync your iPad to your PC to get your latest purchases or can you do that via the wireless connection directly on the iPad after the initial set-up?
That said, if one of us buys an app/movie, will we both have to carry it on our iPads or will they store remotely on iTunes or on our PCs? I'm just concerned about maxing out the storage space on the iPad. Do the purchases need to occur on your PC vs. the iPad itself for both to have the app/movie access?
I've also read about iCloud issues and syncing all calendar/contact/etc. accounts if two iPads are set-up with the same Apple ID. What's the best way to initially configure the iPads so that you avoid this headache in the future?
Once I get all this settled and get a new iTunes shared account working, is there any way to get the movies I have in both of our old iTunes accounts into the new shared iTunes account? Can I simply drop them on a jump drive from one PC and place them into an appropriate folder on the new PC that the iPad sync's to if it does in fact need to sync?
Again, appreciate all the help and sorry for all of the confusion and multiple thoughts. I would just like to set this thing up once and for all the right way.
Thanks again

1, you can (re-)download a lot of purchases directly on the iPad without having to connect to your computer - apps and ibooks can be re-downloaded (as long as they remain available), music can be re-downloaded in some countries; tv shows can currently only be re-downloaded in the US. Re-downloading
2, films are a one-time only download, so you can either download it on your computer's iTunes and sync it to your device(s), or if you download it directly on the iPad you will need to then copy it to your computer's iTunes (connect the iPad and do File > Transfer Purchases) so that you can make a backup and copy it to your other iPods, iPads etc.
3, I haven't had any problems with iCloud, but then I don't share my account so it's only my account and contacts on my iPad and iPhone.
4, you can authorise your old accounts on your computer's iTunes (Store > Authorise This Computer) and copy the films onto it : File > Add File To Library - you can't copy or transfer content to a different account (nor can you combine accounts), they will remain tied to the original account
The iPad's manual has some info about syncing and each of the built-in apps (the iBooks app is covered in the manual though it isn't pre-installed, but you can download it for free from the store) - the manual can be downloaded from here http://support.apple.com/manuals/#ipad

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Setting up Brand New iPad 2 - iTunes Sharing and Getting Files from old iTunes Account

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