So, here's the problem I've had to face. I have iPhone 2G with an older iOS version and iPad 1 with one of the most recent iOS versions.
The problem is that some software is designed to work both for iPhone and iPad but iTunes is rather dumb about recognizing the fact that the newest software isn't always a good choice in my case. My older iPhone simply can't run that most recent version of Skype or whatnot.
Esentially, I have to either compromise and decide what device gets the newest update for this or that software or juggle around with swapping ipa files to update each device in turn. Now, I'm not really intimidated by that but I wonder how most people who are not that technologically savvy deal with this?
Do you know people of any other way to have two or more different versions of software in iTunes library to sync different devices without having to intervene in the process to extent of extracting ipa files from filesystem path and placing the needed version of software to update each device in turn?