Wireless sync with multiple devices? + related q

Does anyone know what happens if you have multiple devices (with different content - but using the same library) set up on automatic wireless sync? My husband has successfully set up his iPhone to sync, but I'm nervous of doing the same for my iPad in case it causes some kind of conflict if they're both trying to sync at the same time.
I've searched and couldn't find anything about this.
Also does anyone know what happens if you shut down iTunes/the PC while a device is syncing in this way? My husband often plugs his iPhone into his alarm clock to charge while I'm still working on the PC, so it's doing the auto sync when he does that. If I don't notice and shut down the PC before it's finished, will that cause a problem?
Cheers

Thank you a lot Jolly Giant, and I have manual sync.
It seems that there is no way to keep an older version of the same app. Is this correct? I never directly replaced older version with newer version, but I suppose it did so when I did "transfer purchases" from iPad. Then it synced the app on older iPod, and it's not really like I have a choice: if I check its name, it syncs and I have the newer version which does not work. If I uncheck, it removes it from the device altogether.
Does not iTunes realize that I have two devices? Both are registered, etc. etc. can it not keep track of minimal system requirements? In fact it appears it's worse than this, older version are totally not allowed, even if someone has by chance the older file, iTunes will not allow.
And it is not like I have a legacy device, this iPod, even though it can not even run the latest iOS (that is, Apple dropped support after 4.2.1 on Nov 22, 2010), was sold new, and not for a cheap price, not so long ago.... btw branded as "third generation" (not everyone is familiar with hardware specs and technical sheets).
The problem will worsen the day my iPad will eventually abandon 4.2.1 in favor of a newer iOS and sure enough there will be newer versions of apps that no longer support 4.2.1 and which so far, I don't download, but in the future I will want to download for the newer device.
Thank you a lot Jolly Giant for your help and thank you to anyone who will help.
Daniela

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