I think the real question is "Which to do first?"
The one day "y'all come visit, now" would be easiest to organize the soonest. I think the required minimum number of participants could be met for most times of the year.
Have CW send an email message to poll for preferred dates, this will get the question to more users.
Meanwhile, back at the ranch, have the tour planners working on the drive-about.
Many years ago one of the CW dudes visited Lansing. It was well attended given we did not have a user's group to help coordinate. And it was only for a couple of hours. It was a quick overview of the new version of Sonar. Too short to ask many questions. It was hosted by a local music store in their 50 seat performance room.
I will pay for a full day of demonstrations of Sonar, some Tascam equipment,... Hold it in Detroit which is drivable for me. Chicago would require an overnight, so I would go there for a two event.
Lansing would be less expensive, easier to get around, and is within driving distance of about 7 million Michigan residents. Gotta be enough attendees to pay for at least a day. Work with the local music stores (Marshall Music), and national stores (Guitar Center is less than an eight mile from Marshall), make it part of a Gibson/Tascam/Cakewalk national tour and Bob's Yer Uncle.
I would attend such even if THE CRAIG was not present.
Many years ago (for three years) we hosted a three day event for Custom Installers in the Union Building on the MSU campus in East Lansing. Relevant vendors came to demonstrate and provide in-depth training. Around 100 dudes attended. This paid for the building, the banquet (with speaker) and some of the daily refreshments. It was less crazy than the big shows and all left having learned and connected.
So I vote for all three.
My main concern is exhausting THE CRAIG and exposing him to the additional dangers found outside his place of confinement.