Living through the evolution of the Web, it looks like money (especially ad money) and social networks encouraging people to broadcast their real identities (often doing so can be lucrative—see both traditional and Internet celebrities' use of Twitter, for example) are the main causes of (negative) changes.

Manipulative ad-spam typo-squatter sites basically took over the Web. Around '08 or '09 Google seemingly surrendered in the battle against them and took to just showing the same handful of trustworthy sites for most searches. Smaller communities and sites faded. Meanwhile, a huge percentage of "legitimate" sites have become nearly indistinguishable from ad-spam sites. The spammers won, in a way, by becoming the Web.

Youtube, briefly a kind of miracle of the information age, is so full of people trying to sell things or make a living at it that they've drowned out the earnest amateurs. Plus there's tons of advertising on it now. Just another bazaar full of haggling and people trying to pick your pocket, where once there was something like a community theater.

Broadcasting one's identity is valuable ($$$) but leads to the ongoing conflict between those embracing that and those viciously trolling them under what remains of traditional Internet anonymity. Now that there's money behind it, the old-school Internet reaction of "well yeah, why the hell did you put your real name and address on the Internet?" is being seriously challenged, even in tech circles, by "real names for all so we can hunt the trolls (oh, also anyone else we don't like, but surely that will never be a problem)!" The money in tying Web identities to real identities may well win, over the value of (even semi-)anonymous speech.

I don't see it as frontier versus civilization: I see it as pure human (and human-scale) expression versus (incomprehensibly massive and alienating) commercial exploitation. Commercial exploitation is winning.