With OP's credentials, he and the 690 would be just fine imo.
I've only managed day rides so far and our first scheduled long ride will be the LA to Vegas in November. I'm taking the slow route to setup the bike toward that ride. If you dial in the controls, seat, pegs, tires, gearing etc and get your gear planned/packed, there's guys running 690's across Africa, South America, Russia... a bike of many uses.
I end up doing the trailering thing about half of the time as well but by trailering, I mean a truck (sry Dr!). Get to the adventure, have it, change and hit drive-thru on the way home. However, these bikes are ideal for getting from 'here' to 'there' when there's mostly dirt in between and I'm planning on using it for that as well.