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Hi Brandon, I am a beginner also. I’be done 30-day and 5-day and am about a month into daily challenges. I have the exact same problems: spending a long time understanding what Tony is actually doing, rewinding, etc. I agree that it can get really demoralizing.
What has helped me is understanding that Tony’s students are on a very wide range of expertise. Many are recycling through for 2nd or 5th year. We newbies only need to work on the very first part of any challenge. It will come back around and then we will master another bit of that skill.
Also, I have found simple songs that I like, learnt the chords, played them on YouTube (over and over) and try to keep up with the chord changes. I.have gone to other YT teachers to learn strumming patterns.
I have had moments of wanting to give up. I absolutely know I would regret it!
Best of luck