It should be noted that certain countries have outlawed the practice of non-transferable software licenses (or so I have read). I am unsure if Belgium (where the OP has listed as their location) is one of those countries. It is my understanding that Cakewalk, for obvious reasons, lifts the no transfer policy where applicable by law.
So essentially if your local laws prohibit such "one owner per license" EULA restrictions then yes, you can do as you please without risk of legal consequences.
In the case of leaving your studio and software licenses to your kids after you shuffle off from this mortal coil I don't think the Bakers are litigious/vindictive enough to launch such callous attacks. Perhaps their new parent company might go down that route but I doubt that as well.
Now if you were SELLING it (in an area without legal protections from EULA restrictions)... then that gets into skeevy territory and could (and deservedly so) incur legal ramifications.
However you could perhaps set the license up under a "business" as an asset. So the person does not own the license... the studio does. Then with a purchase or transfer of the business and all it's assets to a new owner it might be legally acceptable.
However I am not a law talking guy.
Contact customer support directly or your attorney if you need specific details on the legality of such things.
PS: I would also imagine that Cakewalk would prefer to have continued customer as opposed to no customer at all. These types of terms are usually implemented to deter flagrant abuse such as software "tourists" who purchase, install then sell programs at a whim abusively or to avoid legal action themselves due to distribution agreements with retailers (and of course to avoid cutting into their own bottom line).
Not encouraging this behavior though. Of course it's best to just buy them their own licenses... preferably while you are still alive so you can pass on the most valuable commodity of all. Knowledge or how it all works and just spending some quality time with the recipient.