> EDIT: and of course actual physical copies of the games are probably the best way to go if possible.
In terms of logistics, physical copies are the worst possible way to play. They have benefits if you're playing as a bonding activity, since everyone has to be there. They have absolutely no benefits, and enormous drawbacks, if you're playing to play.
Digital games do have their advantages, but that's going a bit too far.
Is it possible for someone can't programming to create a digital game? Could they implement "house rules" on an existing game? In games that have trading, how about non-standard trading? (Eg I've played Settlers with futures) How about granting a younger player an advantage to compensate (eg, give them an extra $1000 to start)?
How immune to cheating is Vassal? If the digital copy runs on Windows, a bunch of my friends already have a copy of ollydbg installed. Is there also a feasible to detect if there's a Excel spreadsheet or Google Doc open that tallying all thes cards used and other information about the game state, and spitting out the odds that my next card is going to be the one I'm looking for?
Meanwhile, playing a game locally means playing with others humans with similarly limited memory and processing power, which means my naive gameplay, which doesn't have the odds of every possible combination of cards memorized, isn't a game of Humans vs. Cylons. (Not that I understand the attraction to online poker either.) Is there any guarantee that the person on the other end isn't grepping /usr/share/dict/words in our digital Boggle game?
Teaching people how to play ("customized live interactive tutorial") is far better with a (patient) real person rather than a recorded tutorial, especially when the game hasn't been translated.
Are you going to be able to dig up a digital copy in 30 years and play that on the latest computer?
Can you give your digital copy to a friend?
How many copies of the game do you need to buy for everyone to play? Most online games require each person to buy their own copy, but aside from Magic and other CCG, the box and some friends is all you need.
That's just off the top of my head. I'm sure you can come up with other advantages that physical copies of the game have.
In terms of logistics, physical copies are the worst possible way to play. They have benefits if you're playing as a bonding activity, since everyone has to be there. They have absolutely no benefits, and enormous drawbacks, if you're playing to play.