@indiescripter I think you've probably got a pretty good start on the IndieWeb philosophy. And an even better start in that you're writing your thoughts on your own website first and then syndicating them to silos like Twitter.

I think that part of what you're missing about being able to reply to Aaron's original post is that his site both sends and accepts a new web protocol known as Webmention (http://indieweb.org/webmention). Thus on his original post, you'll see that I've "liked" it by making a post on my own site (http://stream.boffosocko.com/2016/liked-aaron-pareckis-100-days-of-indieweb-147eda7b83), and then in the background sending a webmention from my server to his to notify him about it. He can then decide whether or not to accept and/or display it (in this case mine appears next to his star icon at the bottom of the post). For the likes and comments/replies on his post, you can hover and find the permalinks for all of the responses on other people's originating sites. I'm sure yours would have shown up too, but I suspect that your site isn't sending webmentions yet, so his site is unaware that your post exists. I'm sure he'll have seen the Twitter response you gave though.

I know Aaron also often syndicates copies of his posts to Twitter. There's another IndieWeb related service known as Brid.gy which bootstraps webmentions onto Twitter (in addition to other social silos) so that replies or comments to the copy that got syndicated to Twitter also send copies to the original post. In this case, he only syndicated it to news.indieweb.org, so it was less simple for you to have interacted with his post because there wasn't a Twitter version for you to interact with.

You'll find that within the broader community that different members will support varying levels of functionality (based mostly on what they're interested in), so someone like Tantek (tantek.com) will post on his own site and syndicate to Twitter, but he doesn't yet display webmentions. You can, however, post your replies to him on your own site and syndicate them to Twitter (perhaps using Brid.gy publish?) to reply to his syndicated copy on Twitter where he'll see the notification of your reply. You yourself serve as another example as you don't (yet?) offer a comment field on your own post. Perhaps you may never, but that's your choice. (I'll mention incidentally that many static website owners are using Aaron's Webmention.io for sending/receiving webmentions, see also: https://indieweb.org/webmention.io.)

I think that a lot of the goal is to not only have fun with what you're doing on your own website, but do things which you find interesting/useful for yourself. Are you interested in locations/check-ins [http://indieweb.org/location]? Reading related posts [http://indieweb.org/read]? Maybe other types of status updates [http://indieweb.org/posts]? Always work on your own itches [http://indieweb.org/itch] first.

Just be careful, because lurking in IRC or browsing the IndieWeb wiki for a while and seeing what others are working on or doing can make you very "itchy". Though the reverse is true that seeing what others have done (even how silos have done things in the past) can make it easier for you to build it not only better, but perhaps more quickly. Perhaps the CMS or language you're using is being used by others in the community [http://indieweb.org/projects]? This may make it easier for you to go farther/faster by using their opensource code, or perhaps make it better by contributing some of your own thoughts/feedback/code?

Keep up the search, and let us know if we can be of further help/assistance.