For big trips, you might consider a travel planning service that walks you through many of the steps above; check out Triporama.com, TripIt.com, TripHub.com, Groupon.com, LivingSocial.com and PayDivvy.com (for divvying up expenses). There are apps for some of these as well.
In the end, while the original intention was to travel as a roving horde, the large group sitting around the living room ultimately split off into a handful of smaller groups — pretty much the same individuals who were most comfortable at dinner together, or when walking around, or when picking roommates. That is, everyone went for their comfort zone, which has its own rewards. But the living room exercise was hardly for naught; on multiple occasions over the next few days, the groups stumbled across one another unexpectedly in pursuit of common interests, and the recombined groups showed a powerfully increased energy level. Everyone got to do what they wanted, sometimes on their own, sometimes together — and always the better for it.
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