I think you did a good job creating a comprehensive and detailed letter that tackled a lot of different activities that you're planning on participating in. On a personal level, I was also happy to hear that your experience with "Invalid Item"  was so positive! I hope you have the same this year with either that contest again, or with "Invalid Item" .

The back-and-forth argument with yourself was an interesting technique, and I'm all for injecting something fresh and unusual into Dear Me entries, but I'm not sure this one entirely worked. It started to feel, to me personally, a little repetitive to read toward the end, and the tone - at times - felt overly self-critical.

Overall, this was a well-written and thorough Dear Me entry. Nice work!