I have a solid regular group, and I was wondering how other people play the Crossroads phase with that many players ?

I don't have Daybreak yet otherwise we would be using Earth, Kobol is dull, and as for New Caprica that's not played at all.

My idea is that the last player rolls a die and uses that persons Crossroad card.

My other question is regards Allies, last night on Vassal we had a player in Sickbay who met Doc Cottle, his trauma was a Disaster token, that player stayed in Sickbay, I thought when you meet an Ally he moves you out of Sickbay/or you move out voluntarily ?

Regarding Sick Bay... You encounted the Ally at the END of your movement step. So you would have to remain in sick bay to encounter him (and you might want to). If you get disaster symbol, the card has no effect (discarded and draw new one etc). I guess you are now sitting in sickbay and proceed to your action step? Never thought of that but I guess it is a small risk to have the encounter.