Is there a way to show more than one region at once? at least with the OSM updates anyway?I do not believe there is a way to load more than one map onto Basecamp, at least when I looked at it a couple of years ago. This is mainly because the file name must be a specific, therefore cannot be duplicated.
What is your preference for using Basecamp versus some of the online mapping tools such as Ride with GPS, Strava, or Garmin Connect?
Aside from fast, responsive, & friendly user interface, Ride with GPS allows for choosing among many available maps: Google, OSM, OSM bicycle, OSM outdoor, satellite, topo, etc.
Strava, on the other hand, allows you to choose routes base on heat maps that show most popular & used routes.