Yeah, so I'd be lying if I said I wasn't looking at pinnacle a little bit for me too. I do love the setting and I've been up and down Washington enough times (rain, snow, warm, cold, sunny, can't see) that I'm not concerned about time or which trail to use. I've thought about some of the routes I've been on, Standard on WH, Funhouse (finished on the Book), the WG ridge which is what I really want to take him up. I'm just not comfortable teaching someone on Cannon. I don't know why so don't ask, Cannon just makes me feel small.
Would Pinnicle be a poor choice or is it as you said Dave, Cathedral has a more opportunities closer together, easy approch/descent etc.
I guess it may come down to seeing what the day feels like on the way up.