This is a great thread! I came to CtC without a specific problem to solve but found the original YouTube series so much fun and resonant with my own experience during 80s/90s that I wanted to continue the journey. I decided to basically work through everything in the order presented on the site, starting with seminars and then interviews (just working those in alphabetical). This approach satisfies my OCD and also takes advantage of something like a cumulative build of knowledge: Volcano + Cascade (go deep into USX), Antigravity (same for double escape), Metronomic (surprise, you can rip DSX even though you thought otherwise). I transitioned to interviews before Obsidian but doing this one a la carte now.
The seminar format is fun and awesome. My approach was to work through every clip example using the tab (and saving the .gp for anything longer than a few bars of more complicated melody). The order of the individual lessons and clips is, unsurprisingly, not haphazard so taking this approach provides a nice build ramp as you study a specific technique. What you will find is that there are some specific clips that make great exercises (e.g., Gilbert Lick, Yngwie Sixes, EJ Atom are obvious but you will come across many others). Those become couch exercises where you thank your significant other for sitting next to you watching TV while you Vinnie Moore her to death and drive those atomic patterns deep into motor memory until they become nervous tics. Pick fun clips that are melodic (there are plenty of them) and you will find that you carry them with you long after you have moved on. Marvel as they mysteriously appear in your improv! Also, don’t skip the Notes on the lessons, esp. Cascade. They are not just transcriptions of monologues but new/additional info and context written in Troy’s style which is a blast to read.
The interviews are also incredibly useful but when I started working through them I did not realize how they would be useful. What is esp. cool about interviews is that you get to see the ideas/concepts your are studying viewed through the lens of different guitar styles and realize that the foundational problems that CtC is approaching are truly foundational. Also, the interviews typically go beyond just picking technique and get into questions like “What does it mean to improvise? What are you really doing in the moment?” and “How does music theory support/enhance your playing?”. You’ll notice that the earliest interviews are more technically focused but once a lot of the fundamentals of CtC are worked out, the interviews start to go way beyond technique. The examples here are also great but instead of working through all of them (there can be 100’s/interview), I pick the ones that are either extremely odd/interesting and probably have some unanticipated benefit (lots of these in Marshall Harrison for some reason) or things I specifically want to work on. I have also really benefited from cross training the acoustic guitar/flatpicking interview examples, esp. Molly, Andy, and Carl. Practicing any of the roll patterns is esp. helpful. Not sure on the mechanics of why this is so useful but it feels a little like baseball batters warming up with bat donut weights before stepping into the box (do they still do this?!).
If you are interested in the “work all the excecises” approach just DM me on platform and I will send you the google sheet i used to track progress that contains all the clip links. Even if you are not as neurotic as I am you will enjoy all the material on the site – it is an exceptionally valuable guitar pedagogy tool and you are in the right place. Good luck!