..having worked in the media at one time
I'd be willing to bet that the "single individual", was under pressure from the management to get the mentioned expansion done asap and with an unrealistic budget.
The media outlets I worked for all had software licence violations of one type or another, for similar reasons.
It can by very "tempting" to just install the apps as needed.
That doesn't condone it though.
Don't Autodesk and Avid still use dongles ?
If so... they had to do more than simply install the apps with the same registration code. A bit more... "intent"