> Would it kill companies to be honest and upfront about these sorts of issues? I feel like "Hey, we're unable to pay our bills unless we can better monetize our product" comes across a lot more honest and trust-worthy than this

The problem is that it's almost never that.

It's not "we're unable to pay our bills". It's "we've got more money than we need already, but we think we could get a lot more this way".

You think, say, Netflix is a struggling business and that's why they have to put more ads than before? No. In a capitalist system, leaving money off the table is increasingly unjustifiable as the number you're leaving off grows. Docker absolutely is in that same situation.