Sir Matticus: Considering Bill Gates and Steve Jobs may be (or were, RIP) in your father's age bracket -- consider that generation 'digital pioneers,' unlike the digital natives of today. When's the last time indeed....pffft. :)
Did you all go out for pi later?
The obvious answer is leadership, but I think it has more of a nuance than that, more akin to what keeps a friendship or a marriage together. It's understanding that there will be times of discontinuity and personal squabbles, but overall, the old tried-and-true values of love, respect, and above all else, a sense of humor go a long way. Managing expectations is true in any relationship, and that comes from clear communication. Easy to say, but tough to do, as most things.
Yes, YES!
Hope this helps: http://wowsugar.blogspot.com/2012/09/watchdogs-of-azeroth.html
Why is it the short posts that sometimes generate the most thought? It is a tough call, isn't it? Deciding to have "every boat float" with rolls of the dice, or sitting in analysis and judgment of resource distribution is something a GM should set forth a framework or protocol prior to the construction of a team, perhaps? And yes, you will make folks unhappy, because the "game" isn't always fair. You try to be equal, but being fair is nearly impossible with the RNGs fingers muddying up the paint.
Tell them you will cut the baby in half? (The "go all Biblical on their fannies" option.)
No hesitation - 2 ten-man teams, and possibly a third for alts. Seems that allows more room for leadership and play flexibility.