Workingman's Dead is a classic, no doubt. When I heard it, it too sounded like it was at least in part inspired by the second Band album. The songs, the harmonies, the country feel. The Band and The Dead (as well as Janis Joplin & Big Brother) did a tour across Canada together, traveling in a train car. Too bad THAT wasn't videotaped! Though not thought of as part of the Rock 'n' Roll drug crowd like The Dead, three members of The Band did indulge pretty heavily, even in heroin.
Bobby Fuller had two different drummers, both good. The first place I visited when I moved to L.A. was Forest Lawn Cemetery, to pay my respects to Bobby. Anyone who does likewise, he is listed as Robert Fuller.