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Jeremy, Like you, I had some of the same issues and questions when I first started. I'd had a primary website for a while that was a bit more blog-ish on WordPress with a few other subsidiary sites for work related things. When I got into IndieWeb, WithKnown had a great plug-and play set up for almost everything, so for me, it made a nice easy place to start. I also wanted to play with Known and use it to get my feet wet. I was particularly interested in owning a lot of the shorter form posting/microblogging like Twitter without overwhelming my prior subscribers on my WordPress blog with a lot of shorter "fluff". Once I'd gotten a few things working, Known was also incredibly good at quick short posts using bookmarklets (or this mobile solution I'd come up with: ). Initially the big difference between my sites was where I stored longer form content and shorter form.

Slowly over time, as I've been adding bits and pieces here and there to my WordPress set up, it has been owning more and more while somewhat less lives on my Known Install. There's also been a huge amount of community development on the WordPress side, so that it's tremendously better now than it was when I started and continues to grow. I think I hit a bigger turning point after IndieWebCamp LA when I was able to work out a bit more about how I want to own and syndicate things from my primary hub (on WordPress). (See also: which has some thoughts about adding RSS feeds from one site to cover multiple other sites). The nice part about owning your own site is that you get to figure out what to do with it and you can literally do almost anything. For example, very shortly I'm about to attempt to own all of my checkins on my WordPress site instead of on Known as I've got almost all the moving pieces to do it in a way I like.

Ultimately, I'd recommend doing what works best for you at the moment as there are literally hundreds/thousands of ways to pull it off. Do things one at a time in small bite-sized chunks until you have it the way you want it. There's no reason to do everything all at once. Sometimes I've found that creating posts literally by hand in raw html has been a great way to start to see both how it looks/works, and then use that experience to figure out how to best/most easily automate it going forward.

I'll also note that my coding skills were old and rusty and have been slowly getting better over time as each piece evolves. Another nice part of the process is that you'll have a chance to see how others are doing things with examples from the wiki to help you figure out what might work best for you. Over the process I've also seen others stop, change gears, and even platforms, and try out something totally different. The key seems to be to start with something you know and begin working from there based on your particular "itches" and needs []. Document in the wiki pages what works for you and what doesn't and why to help others along the way. What works for you won't necessarily be the best solution for others and vice-versa, but there's lots of examples out there to work off of.

Your post was certainly a good start for taking stock of what you've got and where you might like to go. Now just make a list of your itches and do things a step at a time. I know there's an IndieWeb Cat [] and an IndieWeb Library [], so I'm glad to think that there might be some IndieWeb bread out there soon too. (This reminds me that I want to get back to microformats for recipes again in relation to JetPack's shortcode work:

Good luck!