If a strom is his future, I would suggest the V2 with a spring upgrade in the near future. Solo at 320 the WEE would happily pull him to the end of the earth, adding a larger passenger and luggage, I am not so sure. Now my goldwing can pull a house (or 2) but even that would need a rear spring upgrade.
There are 10 types of people, those who know binary and those who don't.
What I ride now:
2013 Honda GoldWing (The Lady)
2014 V-strom 650 (The Mistress)
Previously: 07 Ultra Classic, 95 Softail, 80 gs450l