Because innovation dies the minute licensing gets involved.
My workplace runs several VMMs for clients (ESXi, Hyper-V, etc) - because each Windows guest system needs licensing and has costs, clients spin up as few as possible, shooting the advantages of having services partitioned off right in the foot.
In my head, Waldo is a trans guy, living his best life, using his dead name Carmen Sandiego, drag, and gender norms as an effective tool as an effective shield against the authorities to seperate their work life from their personal life.
This is why Carmen is flashy, memorable, and bold while Waldo is quiet and casual.