Thanks for the welcome and encouragement. Our goal is to be proficient and comfortable enough to take the tandem on Pedal Across Lower Michigan (PALM) in late June. This is a 6 day bicycle tour across the state of Michigan, averaging about 45 miles per day.
The biggest things we need to work on, as agreed by the both of us, are getting comfortable enough in the handling to ride comfortably with traffic and getting the fit dialed in. For the fit, we are replacing both handlebars (risers for her - she's coming from a comfort bike, and On-One Mary bars for me), and then general fine tuning of saddle and bar position.
We figured out pretty quickly that we don't do well with her being on the bike to start. We had great success with having our right feet on the pedals (in the power position), and both kicking off with our left feet.
I only missed calling out one major bump, and it caught me by suprise even. There were a lot of little chatter bumps that got annoying after a while (due to the fact the rail-trail is shared with horses). My wife doesn't care for the motion of a suspension seatpost, but I'm thinking we may try a sprung saddle for her.