It seems like you don't have a very broad exposure to closed source development.
Probably not. 15 years is not that long, what do I know, I'm just on senior expert level.
Companies run skeleton crews on crap products that don't make money. Stuff they give away for free or that's only used by legacy customers. Stuff they can't shutdown because of contracts or because it still making a bit of money.
You might notice if you get escalated to development enough that it's always like the same guy or two. It's because they might only have a couple of guys working on it.
This is where your lack of knowledge about products like that shines through. It's common to only get the same guy or two, because that's the people designated (or willing) to talk to customers.
In real life, OpenSSL was run by a single person. That's not a skeletton crew, that's abandonment.
From what you are writing you aren't a programmer and you haven't worked in a software corporation before, but instead just extrapolate from your experiences with customer support.
