Deedolce- 1st I would tell you that if you would like a chance at the summit, do the South Side first as it is inifinitely easier (all up but more flat areas) than the North Side which is up up up once you get into the canyon.
I like doing both sides, I'm strong enough to do the summit either way. However, I'm less tired from the South Side and a bit faster as well.
How many in our group?- Depends on what day of the week. If I get an email out in the next few days we'd probably be a gang of 7. We'd start at Heather Farms- since you know the area, I trust you know how to get there. As I said before, the option for N or S is easier if you start there since it is so close to the Iron Horse trail (we always come back via the N as food calls at the end!) People ride their own pace- it's always YOUR ride.
If indeed my buddies consent to Friday instead of a different day next week, you will have the honor of escorting our oldest rider Joe Shami. He's now done 39 weeks in a row and still cranking. He's quite a character as you might imagine. He would be riding over from Lafayette to meet us.
Do let us know a confirmation of the dates and then I'll get the word out to my friends too.