This is unusually insightful for a LinkedIn post. One question, though: towards the end, it suggests that GPL/AGPL products, which are more defensible against commercial competitors who simply resell the open source project, are "legally murky" and might be rejected by customer legal teams. But does that matter? Can't you just do what Sleepycat did, and offer commercial customers a clean commercial license?
It isn't an issue of "clean"; GPL/AGPL aren't "legally murky". (Though if a customer is willing to pay you because they think otherwise, by all means.) But if they're "rejected by customer legal teams", that's an opportunity to sell an alternative license or exception. I've collaborated with the legal teams at various companies that review both inbound and outbound FOSS. Inbound, there's no open legal question with GPL-family licenses; they're only "rejected" in cases where they're functioning as intended and that isn't desired. (That includes companies that systematically reject AGPL; they're concerned about the license working as intended.) Outbound, the pressure to not use GPL-family licenses when a choice is available doesn't come from the legal department; it comes from product teams who don't seriously consider copyleft and what benefit they might gain from using it, because all the other teams they see are using Apache or MIT or BSD. And then those same teams become shocked when their own code is used to compete with them.
There's a strong tendency towards "do what other people are doing", and there are a lot of companies releasing permissively licensed code. This seems self-defeating.