@khurtwilliams A bunch of us are working on making it all easier in steps, but we're also doing it on a volunteer basis. Some of the key is knowing what it all comprises from a top-down perspective, then knowing what each of the individual pieces are and how they work. Nearly every week there's something new and cool. The key is to figure out which things you find the most useful and valuable and work on those one at a time.
It's a LOT easier now that it was even 8 months ago and will be measurably easier as time goes by. I'm currently writing a book on how to do it all at the level of "IndieWeb with WordPress for Dummies". Ideally it'll be as easy to do as signing up for a Twitter or Facebook account and just going, but we're not quite there yet, but it's getting easier to do the set up without knowing a lot of (or any) code. Hoping into the chat, going to a Homebrew Website Club or IndieWebCamp can be immeasurably helpful as well.
Again, if you want to do a quick conference call/video chat, I'm happy to help you out.