The time for I2P comes when people bring it, I think. If we think of I2P as like the internet, then what brings about it's time is applications that popularize it. I'm not sure what that application or group of applications will be, but a better way to configure and launch browsers on multiple platforms might be part of it, and obviating the installation of the JVM/OpenJDK for Windows users is a part of it too.

Mixing social elements and peer-to-peer file sharing might be another, like a f2f microblog/messenger/torrent tracker for sharing files privately. Sharing a single b32 for every peer would have to go though, I would use Magic Wormhole to generate a short phrase which contains a link to the real b32 gateway to their node. Or somebody who has more time/likes node better than me could port WebTorrent, that would bring us all the really awesome stuff that people build on top of WebTorrent all of which is incredibly cool and useful. I really want to see more games, even simple ones. Chess, checkers, backgammon, either using traditional chess servers or something modified to be peer-to-peer. Freeciv long-turn games. Up to a point, even real-time games are possible with short, multipath tunnels. Games are neat because they occupy a social context which is not widely considered a part of the anonymous internet, even though major services have emerged and been successful in marketplaces largely because of things that happen because gaming is not tenably anonymous.

What I think these all share is a tendency to be "Fun," the ability to be "Easy," and for that to produce a "Network Effect." People don't join networks to talk to no one. Sometimes they join networks to talk to themselves, but mostly they want to do things with other people. Finding new ways to facilitate people doing new things with other people is what I think grows I2P.