I think Ian is right about traffic and start time.
A 9am ride start might be ok, but the later we go the busier the roads will be. Bear in mind the tourists we will be sharing the roads with will be looking everywhere but at the road!
Pooley Bridge is a short distance from transition and has a number of small car parks in the village and the bridge is a central meeting point. It is also at the quieter end of the lakes.
Getting to Pooley Bridge is also easy (5 miles from M6 J40) and completely avoids the tourist choked south lakes.
If the route order isn't too important to folks, George's idea to start near Kendal would mean we get the busiest part of the ride done first (Kendal - Glenridding) and does shorten the drive by about 1/2hr.
Having said all this, I'm relaxed about where and when.
Ben
PS Stuck in hotel near Stonehenge for the week, so no training with Man Tri this week

The greatest danger for most of us is not that our aim is too high and we miss it, but that it is too low and we reach it.
Buonarroti Michelangelo (1475-1564)