Syncing devices to multiple iTunes accounts on multiple computers.

I have 3 computers in my house, 2 belong to my sister, 1 is mine. Mine is very old and failing so I am probably going to get a new one. Before I do that I would like to preform a complete system restore, I hear that sometimes helps fix the bugs computers accumulate as they age. The problem is I've never done this before and I worry that I might loose valuable information. I keep everything I own on a 500GB external harddrive, so the only things that are really at risk are my Google Chrome bookmarks and my iTunes Library. Everything else I can just recover from the E-HD, but those two... I am still not sure how I can back them up. For this thread I will focus specifically on my iTunes Library though, and leave the Chrome dilema for another day (and another discussion forum).
I figured that if my old comp does go belly up I could always sync my stuff to one of my sister's computers. She mainly uses her laptop and she has told me I could use her tower to sync my iPod Touch and my iPad if I need to. I would be able to use her tower at least until I get myself a new one.
I've found several guides on how to backup the iTunes Library and metadata, and I have tried to do so. I transfer my songs and the backed up library onto a flash drive and then plug them into the new computer (my sister's comp). I drag and drop it onto the desktop, and then plug in the Touch. Oh yea, I feel I should mention something here, I'm going to try and preform a transfer of the iTouche's data first, then continue with my iPad depending on how that goes. My iPad has become my agenda, I use it for everything. And accidentally loosing all my contact/agenda info because of a botched attempt at backing up it's library is NOT an option.
So yea... I try first with the touch.
All the files are there, but when I logged into iTunes he still asked me "You need to reset this device to it's factory parameters before you can sync into this computer." Basically he needs to nuke everything on it so I can't be synced on two computers at once...
I declined the sync and tried to load up the Library I had brought over from my old comp. Problem is... he doesn't offer any option of importing a Library, in the usual spot there's only an option for exporting. Which is idiotic because this iTunes has nothing in it, it's a blank slate.
Then I tried something else, not sure what prompted it, I went on the iTunes store and downloaded a free App. And he was able to put it on the Touch... he asked me for my iTunes account info and password, and then he seemed to indicate my Touch was synced on both computers (and that I had a total of 5 computers I could sync to). The Library still hadn't transfered, since the iTunes on this comp still had no songs, but my Touch still had all 250 songs. So it didn't get wiped...
Basically my question is this. Can my devices (a 2G iPod Touch and a WiFi only 64GB iPad) be synced up to multiple computers, with my main library placed on each of these computers.
And if so, can these Libraries be continually updated with regards to one another through the internet (or at least through my home network). By this I mean, if I make a purchase on one of them, will the other Libraries be updated and get this purchase.

PTNLemay wrote:
I keep everything I own on a 500GB external harddrive, so the only things that are really at risk are my Google Chrome bookmarks and my iTunes Library.
What if that 500Gb drive fails? You need at least two copies on different drives of anything that matters, one just isn't enough.
I use SyncToy 2.1 (free) to keep my backup copies of my iTunes library and other important folders up-to-date. If there's room for the library on the internal then a single external backup is fine, but if your external holds the only copy then you should look to getting a second external drive as backup.
tt2

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