Often, it's trial and error. Sometimes, you can inspect the package using something like Pacifist, and you can tell based on the preinstall/postinstall scripts (i.e. they contain static references to a file or folder location, rather than a relative one). Other times the package is too complex to tell any other way than to try it out without that option and see what happens.
You can assume that Adobe installer packages will expect to be installed to the boot drive, so those would have to be installed after imaging.
As far as "requires restart," again, trial and error. If it installs something like a kernel extension, a launchagent or launchdaemon, or the like, you'll probably want to restart. If it is just an application that doesn't touch much of anything beyond the applications folder, you're probably safe without.
