Sounds like he wanted a second subscription but used his same login info to purchase. I believe he should have created a new SD account for the second subscription, he would have gotten the desired result.
This is a guess on my part as to what he meant to do, I could be wrong.
I have 8 PCs in this house. In order to have Stardock programs on more PCs, without hitting activation limits, I bought a second subscription to ODNT, but I used a second account to do it with.
So, rather than extending my original sub for a year, I now have 2 separate accounts/subscriptions.