Hey rachel
I think it would be a great idea to get Dylan started from Nov'08 onwards? So that you can see how well he might adjust to playgroup/pre-N, if he doesn't, he has some time to adjust (as well as for yourself) the crying, tantrums etc. Also by then, by 3rd trimester, usually energy levels are low, so it would give you some more time to rest and prepare for #2?? So at least come Jan'09, when #2 comes, not too much adjustment for you and dylan. I'm sure dylan will be a super good boy, have seen how well-behaved he is with you and he's matured for his age too!!