"Transfer App" prompt with multiple devices

I own multiple ipads and iphones and try to use the wireless iTunes sync where possible.
One issue I have is the prompt for "Transfer Apps" when syncing. it stays there and unless i happen to check my PC i have no clue that my sync's have basically stalled. Is there anyway to just make this a default setting so it always transfers apps, and I no longer get the prompt?
Thank you,
D.

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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    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.
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