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@Velocio
I've done both, and the noticeable difference is that the 8am lot won't necessarily stop if you get a puncture (know the route before you leave) and will generally do Ranmore (which is a bitch as you might know) and if they're feeling buzzed then they might not even stop at Box Hill café. Which basically means the whole thing is a hard training exercise which they try and do as a group (because they can get more speed that way) but if you get dropped then they will continue with their training.
The 9am lot will go at roughly the same speed, however they will stop for punctures, they will let people catch up on hills, they'll give you the choice of doing Ranmore or not (because they split into two groups just before and re-convene at Box Hill), and they'll stop at Box Hill.
So... same speed but no chance of being left behind or stranded and a lot more support as you go around. The stops means it will take longer, but as it's roughly the same speed you get to see how bad the 8am might be.
Shoot for the 9am unless you know the roads like the back of your hands and think that the hill at the back of Richmond Park is still nothing even after having done 4 laps.