One of the biggest benefits to retirement is that every day is Saturday... When I retired in 2017, the first thing I did was take my ride for a 3 day trip around southern Ontario. I got home then packed the Rocket up for a trip across Canada to visit my son and grandson in Edmonton. Then travelled through part of BC visiting Jasper, Radium Hot Springs, Fernie etc then back home. That was one of the best times I have had. I would like to do it again but the old bones today aren't quite up to the same standard as 2017. The longest rides now are no more than 8 hour day trips a couple of times a year.
One comment about calipers... they are easily rebuildable. Check with Fasteddy sports
https://www.fasteddysports.com/shop/ . He carries a lot of parts for the America/Speedy.