1) I think the OSS landscape has simply changed. We used to have a handful of languages and frameworks with cryptic documentation, which O'Reilly books could coalesce in definitive bibles. Now you have new stuff coming out every day, github repositories all over the place, new tools, languages on top of languages... It's much harder to figure out what matters and what not. In that sense, O'Reilly is holding better than most other publishers, in what is probably a lost war (things will accelerate more and more, to the point where relevant point-in-time documentation will become impossible to produce in book format).
2) I agree on this. I wrote it down to the spirit of "American optimism" that us Europeans can find a bit distasteful, and sometimes it just seems too self-serving, fanning the flames of this or that technological phenomenon in order to sell more books. However, that's his job, and at least he tries to bring some open debate on the topics rather than leaving big players to come out with The Next Big Thing on their own.
3) All O'Reilly eBooks get automatically synchronised to your Dropbox folder in pdf, ePub and Mobi, which I think is a fantastic story for mobile (could do with better Kindle integration I guess, but Amazon holds the keys to that particular kingdom). I've never used Safari tbh, I'm not a fan of subscriptions.