Good article. Gotta say, though, I agree with your wife on the planning aspect. Every time I don't thoroughly plan a trip, I end up missing something that I have heard of, wanted to see, but did not know was on my approximate route. By planning intensely, do I miss some things that a free-form traveler might see? Maybe...but I don't know about those, probably never learn about them, and those have no regrets. I am an inveterate planner (and not just for trips), always have been, and probably always will be; it brings me great comfort.
As for the Grom - well, aside from the ridiculous looks of the bike, and of an adult on one, I would be quite worried about modern fast, distracted traffic, if I was going so slowly. I used to take 20-40 mile rides on a Honda C70 (Passport), top speed just over 40 MPH. I was younger and (probably) more foolish then; now, I just stick to our local road, and lots, pastures, etc. Any further, I take the motorcycle!