As it turns out, I feel pretty good about my last ride, because it was my first venture outside the sanctity of my little neighborhood. It was also the first time I've ridden with a purpose to go somewhere. Finally, it was the first time I felt confident enough to brave traffic (all be it very light traffic). So yeah, over all it went well. There were a few rough edges, but nothing too difficult.
That said, I absolutely love the new jacket I bought. It's a Dainese Santa Monica. Normally, I would consider it way outside the range of what I need for the type of riding I do, but it was on sale. 40% off! The jacket's really quite warm for what it is, and very soft, which is a wonderful feature of motorcycle jackets as they're supposed to be snug. Overall, I'm very happy with this somewhat overly expensive purchase. Bonus though, it just looks pretty hot, so how could I not love it.