We have an older Co-Pilot with rim brakes. We have about 13k miles on it. The brakes work great. I've never wished for disk brakes.
Packing and unpacking a coupled tandem is a big project. It is doable but not quick. Especially if you take care not to scratch the paint. Even if you are practiced I'd guess it is at least a 2 hour project at both ends. For that reason I think a Tandem Tuesday would be much easier.