Just a short update for anyone interested. I finally managed to do a longer ride with a more experience friend of mine. We ended up doing 35 miles on a dull but cool southern California morning. It was surprisingly easy, what I mean is I didn't flake or stop apart from stretching our legs. My hill work commuting seems to have paid off, as those were less of an issue for me.

All in all, a very enjoyable session with another to come this weekend. Bring on the half century lol