@jason-ashley Welcome to the TAC community. Great question.
The way I look at it is if you have prior guitar experience, then you can jump into the daily challenges anytime, concurrently with taking the 30 days to play and the following Get Started courses It depends on how much time you can commit every day. However, if you’re new to guitar, my suggestion is to complete the 30 days to play, the next 6 chords, and the other suggested Get Started courses. This will get you started and help you to then move to the Dailies and other Skill Courses.
You can jump into the dailies any day. The lessons follow the same daily focus every week. Monday – Technique; Tuesday – Lick; Wednesday Scale/improv; Thursday Rhythm, and Friday – Chord transitions. So if you look at it from just the perspective of the focuses noted, then starting on any day makes more sense. Otherwise, jump in the first Monday that comes up to experience it as a whole.
Hope this added info helps you out.