How to know when a pkg requires "Install on boot drive after imaging" or "Requires restart"?

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.

I realize it's not the best answer, but for me it's usually trial and error.

Typically anything that isn't a simple Applications folder drag and drop install, I setup to install after imaging. As far as requires restart, I usually ignore it for the purposes of imaging since I have a restart at the end of my workflow anyway.

@rcs336 my opinion is similar to @georgecm12 & @hkabik.

I tend to tick that box for all PKG's & I have a restart as part of imaging after they install anyways.

Well thats always but. Thank you all for the quick responses. :)