After much research I think I have decided that the R65 is the best bike for me. I want something that is most months a fun and easy going day tripper or afternoon ride, but once or twice a year can make it to Michigan UP from Chicago.
Current ride is a Triumph Legend TT. Great bike, more than enough power for my style. Main beef is the range for touring is a bit short. I'll be selling that off ASAP and looking for an R65, or maybe same era r80.