Good to see you guys planning something like this. I'm sure that RIBnetters this side of the pond will show some tangible form of support. I will not forget the excellent welcome/assistance we got in the IOM, for example...
A couple of thoughts in no order are:
It would be nice if you could stop over, it enhances the experience and gives crews a chance to R&R. Plus you have no pressure on the return leg, returning earlier in the day, soberish
Weather forecasting is good enough now to give you a secure 36 hour window.. The fact is on a trip like that you have to be ready for the unexpected anyway, many's the boat got left behind...
You can forecast fairly well for wind, but fog is another matter and would be a likely one for you to encounter. You are all big boys and far be it from me to tell any of you how to do a day like that, but I would be thinking along these lines if I was the "organiser" (remember, if anything goes wrong, someone will want to interview the "organiser").
1. Passage plan it and run through the plan at a skipper's meeting before the depart.
2. Marshall it - List boats and PAX, coordinate comms, if there are more than 2-3 boats, designate a lead and sweeper boat - especially if you do decide to run in pairs. I don't like pairs, btw - too easy for them to get separated and there's no backup plan. The last pair, the slow/shaky/tired pair, will be alone...
3. Talk to the Irish CG, they're not overworked and will take an active interest in your crossing, especially if you are a biggish group of small boats. They'll hear your group comms.... I'd phone them and file a TR on the morning. They'll see you right.
If there was enough beer in it for me, I could be induced to deploy a 110 and jerry cans to Wicklow.
That pub looks like a dump, does anyone deffo know it to be otherwise?