Beginnings are always an interesting dance. I’m in two BW games right now: One I’m running and one I’m playing in.
The one I’m running is a campaign/setting I started years ago, but I rebooted it with a whole new group a few years back — new players, new PCs, but the same kicker I used with the original campaign. It’s been really cool to watch the game start in the same place and rapidly begin to diverge as these new players make different choices, fail in different ways, and pursue different beliefs.
With years of play in this setting to draw from (established NPCs, places, etc.), this game tipped more in the GM-directed direction than yours (at least for the first few sessions), though the players have certainly made it their own. When we held our character-creation session, I provided six ready-made affiliations PCs could buy into (they were also free to create their own, as normal). The players didn’t end up buying into any of them, but just seeing them and their interplay provided a lot of fodder for starting beliefs.
The one I’m playing is the 20+ year BWHQ house campaign (those of you who frequented the old forums might remember posts about the adventures of Si Juk, or the Storm King campaign). All the characters are 2nd, 3rd or 4th generation characters (i.e., Si Juk started as the errand-boy of one of the original PCs).
My character is one of the newer ones. I’ve been playing him for about 10 years. For a long while he was the newest character, though we have a few new characters in the current arc. One of the new PCs has been an NPC retainer/bodyguard for a long time, but his master is off doing something else, so he’s come to the fore.
We do 6-24 session arcs every other year or so. Often we play the same characters. Sometimes we play different characters in the same world. Sometimes we do arcs that feature only one or two of the main characters.
Every time we start up again, we do the same dance you described. The characters are familiar, but it’s also been a while and it takes time to adjust to being in their skin again. I think we also tend to be more risk averse with these characters, at least in the first few sessions — it seems a little harder to throw caution to the winds with an old, familiar character.