In practice, I have never once seen this work. Arguably Canonical and Red Hat are the two best examples of CLG/OSS business models, and both of them have uneasy relationships with the greater Open Source community. Canonical is seen and treated as the Microsoft of the Linux world; their promises aren't worth the bits they're delivered on, and they'll sacrifice anything for money. Red Hat is cautiously embraced by the community despite being much more benevolent, usually because their aligned interests don't always consider power users or extensible architecture. They move fast, break things, and forgot to ask your opinion.

Neither Canonical or Red Hat are particularly well-loved by the greater Linux community, for wildly different reasons. At the core of their failure is the illusion of a successful Open Core business (or "freemium" as you put it). The delusional business obsession over ruining the free version of software is exactly why Open Source is so successful where businesses fail. You should research why Linux and BSD won over the alternatives from AT&T and IBM; they didn't have a premium or pro version, they were the pro version. The creation story of GPL, Free Software and Linux as a whole is a warning about how business models collapse when they molest functionality for money.