Licensing on machine with multiple boot volumes of MacOS

I’m currently setting up my next stepping stone machine: a 2016 MacBook Pro with a 2TB drive. I’ve partitioned the internal drive in two, with Monterey on one partition and Mojave on the other. This way, if I need to run software that’s not 64bit compatible, I choose the Mojave partition as the start up volume and boot up with that, otherwise for newer software that needs a newer OS, choose the other partition with Monterey as the startup and boot up with that instead.

The question is: How do you best handle application installation, and how does SketchUp’s licensing technology see this setup? Can you install an app once on one volume and run it from the other volume/OS? If I install SU on both volumes, is that two installations? No matter the boot volume used, it is one machine with one MAC address, and I seem to remember something about the MAC address being the critical thing to legacy app installations. I could just start trying things, and see what happens, but I thought I’d ask first if anyone had any better informed insights.

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Something to think about is whether your older system should be an HFS partition. If it should, I think it won’t see the applications on the APFS partition. There may be other issues too, so I would think about each partition having its own Applications folder, with another copy of the applications you need to run in both systems.

If both systems can be APFS, perhaps it could work with one copy of the applications, I’m not sure.

If you have a classic license, you should be able to add the license to both systems, and it would only be seen as one activation. For subscriptions, there is a unique number set up, that represents each first time you have signed in from that system and that SketchUp version. I think both sign-ins would count, even if the two systems are sharing the application. It’s where the support files are that matters, and those would be inside the two user library folders.