Thanks again, folks. Sage likes views from the top, and she's a pretty good rock scrambler. I guess if we choose Jackson, I'll ask her to walk herself over the rocky bits and spot her on the ledges.
I'm shying away from Tom because Alex and I really want to knock of three peaks at once when we do Tom (with Field and Willey). I can't carry Sage for three peaks, that's just too much for me.
Same with Osceola. When we do that one, we want to do both.
So we'll have to decide between Waumbek and Jackson.
Thanks again for all your input! I appreciate the advice!