Fwiw the mixed content warning is from VideoPress, which is also used in the WordPress.org announcement and also throws the same error. That said, I reported it to the right people and it's likely getting fixed across the board. So while I highly doubt that's what the commenter was referring to, your followup made the web just a bit better, so thanks!
I wrote about a lot of developer facing features and linked to source materials to help folks get more information that are not blogspam at all. I appreciate your feedback on my work though, really; you're such a nice guy.
If I have a friend that can't pay what I find it worth, I usually just do it for free. As soon as someone pulls out their wallet, expectations go way up. Another good tactic I've heard is to put the value price (what you'd charge someone legit) and then discount it to their price, but show it all. Then they value it what it should be.
People build a lot more than blogs with it now. It goes head to head with just about any CMS now, and dominates the broader CMS market. That said, it's just now being included in more enterprise and government style projects.
One downside is that the very platform he is broadcasting on could help pressure cable companies, but is perfectly fat and happy propping them up. HBO is a huge influencer and should join the others against these changes. Though I completely agree with his points.
I think you are short-changing the thoughtfulness of their long term investment partners (especially True Ventures - of which former Automattic CEO Toni is a partner). I also think you are thinking of Matt Mullenweg in the same light as many other startup founders, but he is quite different, especially in regard to his commitment to open source and publicly stated desire for Automattic to be a very long-term company, not reach a high valuation and have a big sale.
Now to your notes:
First, they don't have 20 sales people for VIP. They have less than ten for sure. Probably closer to five.
Second, VIP has more than a 100 customers, by far. And VIP business has grown ever since it was introduced, but simultaneously has become a smaller and smaller part of their overall revenues (I know this to be true). Which means other aspects of their business are growing faster than VIP.
I've followed Automattic closely for a long time. I don't at all see them as the type of company to just grab money in frothy markets. I think we'll see this money equip them to make some much bigger investments in the next couple years. They are certainly in better shape than any other CMS or blogging platform ever has been.
The original post title didn't include the .com, so said "WordPress parent company" which is inaccurate. It was probably submitted to be technically accurate. Now that the post title has been adjusted to include .com, it would make more sense to use that here.
They've been running with positive cash-flow even without the investments. Few employees and relatively low costs. Matt notes in his personal post that they are capital constrained for faster growth but not for operations, so it's not about running out of money but having more money now for current opportunities. http://ma.tt/2014/05/new-funding-for-automattic/
It's pretty acceptable for themes and plugins to expect people to be on the latest version of WordPress, or at worst maybe one version behind. The more complicated support metric is PHP version. Unfortunately, widely used plugins probably still need to support PHP 5.2, because so many hosts won't upgrade their client's PHP versions.
I haven't worked there, but I imagine it's quite different today than it was in the first few years. They are more structured now, though still relatively flat considering the size. It's a team based atmosphere with team leads for each project. Teams rotate as needed, they aren't hard-line departments.
Scott Berkun worked there for over a year and then wrote a book about his experience. Probably as good of a resource you'll find, and a quick read. I reviewed the book here: http://www.poststat.us/year-without-pants/
He was the Founder and "President", but they didn't specifically say Toni would be the new President. Toni ran the day to day though, so that's what I assume Matt will be doing now.
Automattic is the first non-freelance job for many of their employees, but most of them are hardly entry-level like an intern. It's pretty widely considered the premiere place to work in the WordPress ecosystem, given they maintain WordPress.com and their employees are responsible for a considerable amount of the development to the .org project as well.
There are filters to turn off auto-updates easily. Also keep in mind it's currently for minor updates only, which basically never break a site. And in beta and RC testing, there were no hard failures, only some instances where the update stopped because it detected a potential issue. It's a pretty clean setup, and overall really good for the security of millions of websites.