Interesting topic! To answer the question of London, with the stats he mentioned would be either board good! Both boards are amazing but if you surf (just) once a month I don't think you will notice really the difference, they're both tremendously good!
Shapes are different from the 2 boards so you can ask yourself, Do you want a Twinny feeling what you like and mentioned or do you want to have a more all-round minimal style board that you can sup surf in more/all conditions. They will definitely not surf similar, but I think you will notice this if you hope from one board to the other and back in a session and not with some time in between (a month?!).
I personally wouldn't compare the Hipster Twin to the SuperFrank because the SuperFrank is a groveller, it's for small to head high waves, the Hipster Twin and the Destroyer you can take out in almost anything to your abilities. of course you can do the same with the superfrank but I wouldn't recommend it. Worldwide is also a good option and has a better and longer deck pad (over the complete board) as the Destroyer with a bit more surf shape. But it's just what you prefer.
Hipster Twin - I would recommend to intermediate level suppers that want to progress to advanced in waist-high to overhear waves, depending on your abilities the sizing for stability.
Destroyer - I would recommend to beginners, Intermediate and Advanced suppers it's an all-round board, one that rules them all and some say a one board quiver. The pro's would say that the 7'7 is still too big/fat with it's 100 liters and relative big nose so maybe for those out there I wouldn't recommend it. I wrote already in some other threads about it:
www.seabreeze.com.au/forums/Stand-Up-Paddle/Review/Jimmy-Lewis-Destroyer-First-Impressions?page=2The Worldwide - I would recommend it the same as the Destroyer but if you search a bit more surf shape then the destroyer
Superfrank - I would recommend it as a second board for Intermediate and Advanced suppers, so as an addition to the Hipster Twin or the Destroyer would be great, I wouldn't use it as my go-to board but one to play within small to head high waves.
I have tried and surfed all 4 of them but I ended up with 2 destroyers, one for chop 8'0 @115 liters and one for clean conditions 7'7 @ 100 liters.