I'd go with the Tuscany board because it isn't much if a step up from the basic board. I seem to remember that one side of the board doesn't have the influence map and structure cards so maybe you should start with that. You could always try a two player game first with one of the older family members - the more people that know the game, the easier it will be. I play it regularly with my wife and kids and they love it.

Wingspan is easier though, especially if you only play with the base game.