I'm asking because I'm guessing I would be giving them access to my Cakewalk account to allow them to download the upgrade and the time involved to download, install and make sure it's all running.
Yes, I've installed software, but the upgrades are downloads and I may be wrong, you can't download an upgrade unless Cakewalk knows you have something you're already upgrading from. I'm probably only saving about $200, instead of just buying X2 (as I'm upgrading from 7PE) but that's $200 to use on something else.