Jeremy, Congratulations on having your own domain! I was poking around Hypothes.is today and was excited to see that you'd moved over from Genius.
I'm impressed that you specifically mention the IndieWebCamp philosophy, which I've also been using for the past couple of years myself. If you need some help in IndieWeb-ifying your WordPress install, I'd be happy to help, though it's now much, much easier to do than it was even a year ago. Shortly, I'm hoping to finish up a post about the IndieWeb and academia/educational related sites, which might also be helpful, though I'm not sure when that's actually going to be finished.
I'd love nothing more than to have Hypothesis be able to have webmention support so that when people annotate my own pages or reference them across the web, the system would automatically send me a notification of that fact. Are there any coders at Hypothes.is who are also part of the IndieWeb movement who might consider doing this? Is there a way to help suggest this into Hypothes.is's roadmap?
Finally, as a side-note, to help beautify your web presence a bit, you might notice that your photo doesn't show up in the author position in your 2016 theme on single posts. To fix this, you can (create and) use your WordPress.com username/password to create an account on their sister site Gravatar.com. Uploading your preferred photo on Gravatar and linking it to an email will help to automatically populate your photo in both your site and other wordpress sites across the web. To make it work on your site, just go to your user profile in your wordpress install and use the same email address in your user profile as your gravatar account and the system will port your picture across automatically. If necessary, you can use multiple photos and multiple linked email addresses in your gravatar account to vary your photos.
Congratulations again!