So Many Roads was the Jubilee/Category 5 to my ears as well. Happier Times was probably the Carol Ann/Jubilee. My guess is that The Great Flood was the same.
It's so hard lately to tell between the Carol Ann and Van Weelden! The only clue that I have is that Joe says he likes the Carol Ann setup for songs that require a cleaner tone. So a lot of the songs like Happier Times or The Great Flood when he's singing needs that cleaner tone. But I think you are definately pretty close with your guesses!
'67 and '74 Fender Twin Reverbs, '74 Marshall 1987 lead mkII, Metro Superlead 100. Pedals from TC Electronic, Ibanez, Dunlop, BK Butler, Electro-Harmonix, Fulltone, Maestro/Gibson, Loopmaster switching, VoodooLab, Boss. Gibson and Fender guitars, Dimarzio pickups.