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'm not sure why the parent doesn't like it, but I can explain why I don't like it. I think there's a certain group of users who have developed the habit of highlighting while reading to keep their place in scrolling media. At least, that's why I highlight text a lot. For me, the quote box is annoying, but I can see how it might be useful for people who don't highlight text while reading.
I am also one of those who highlights while they read and find this quiet annoying. There seems to be no real reason for the button to start at your mouse pointer and move over to it’s final resting position. Just showing it in its final resting position would decrease the obnoxiousness of it ten fold.