From John Johnston:

Perhaps shorter how-tos that don’t link off too much might and have a smaller scope might help generation 2 & 3? I am not the best person to judge this.
Some friction comes with the power. Especially if you have already got a blog, workflows etc going. I’ve found quite a few assumptions I had were slightly wrong.

And...

as I click Publish, will this end up as a comment on Chris’s post? How will it look on twitter, on micro.blog, I can’t say I am wholly confident that I know!

Then from Eli Mellen:

I wonder if the generations are still applicable and/or useful? Generation 2 is so broadly defined it is difficult to say what "they" need, because as a group of users they're not very clearly articulated.

And from a second post:

I think better on boarding materials and user-friendlier documentation would go a LOOOOONG way. BUT, before one can create such documents there needs to be a relatively stable way of joining the indieweb.

The theme of simplicity and reliability is a recurring one.
Eli does go on to say "Between wordpress and micro.blog I think that is starting to emerge" but this is currently an edge case; we need the support of a major player.
I still think getting indieweb support baked into WordPress core would be one of the quickest routes to adoption.