Matt, there is nothing usual about your upgrade, it's the first one we've attempted with the humcanceller not in the center and with the battery between pickups.
For more regular upgrades, the time is usually 1 month, as long as you send it in at the appointed time. I'm taking appointments for December now, so if you send it in before that, it will likely wait around until we can start.
If you have to bad luck to have your instrument here for an upgrade on the rare occasions that my dad is out ill, nothing is going to happen to it in the upgrade department until he is back at work.
It also does depend on the instrument itself. Some are easy, others are hard. There is no way to tell if a specific instrument will be easy or hard, unless of course there is a brass plate between the pickups, then I can guarantee it's gonna be hard.
Also, if you have brown pickups you want to preserve, that can take a good bit longer as well, since the engineering work can be much harder with the bar-mounted pickups, though not impossible. However, the bar-mount pickups will generally not get as quiet as the 4-hole mounted style ones.