New bike did great. I was a little concerned when we got there because my wife hadn't seen it, except in one picture. And she loves the more retro look of the Classic, rather than the more modern V Star Custom. But when we got there, the previous owner had it in the driveway and he was polishing it. Her first words were, "It's gorgeous!" So passed the first test.
Turned out it was actually 100 miles between Riverview and Casselberry, all on I75 and I4. Previous to that, I had only done about 25 miles on the interstate. World of difference between riding a 325 pound, 500 cc bike on the interstate, and a 625 pound, 1100 cc bike. The V Star handled it perfectly, comfortably doing 75 on the interstate. Even caught myself doing 85 at one point.
Two downsides: First, the V Star stock seat puts me at "GET OFF THE BIKE NOW!" stage at about 100 miles. Second, my wife bought me a high visibility vest to make sure the cagers could see me on the slab.
But the bike got me home with everything but my dignity intact.

Once home, my wife and I took it for a quick ride around town. She loves the much larger passenger pillion on the V Star. Of course, the extra foot of length and longer rake means I need to work more on my slow speed maneuvers with this one. Can't quite throw it around with the ease I could my Shadow.
And when we got it home, she sat on it and discovered she could flat foot it. (She's only 5'0" tall.) If she decides to get her endorsement, I better get her a pretty nice bike, or this one is gone!
And for my other bike related activity, I made ZERO progress on getting the Shadow ready for sale. I'm in Boca the rest of this week, but after that I have to get the Shadow on Craigslist, ASAP!