Don't even think about entering a rowing race in your inflatable, except against a real pumpkin. And your Spindrift is a fine dingy, but it's very small for a serviceable tender for most people. I'd have opted for the 11' too like David did, if not the 12'. But I wouldn't tow any of the Spindrifts much more than I would an inflatable, some dinghys tow poorly(Spindrifts look like excellent rowers). I'd opt for an inflatable on deck instead, too. The Spindrifts wouldn't do well in the conditions I do tow in( I just towed my dinghy to Cape Cod and back, again).
My friends boat is a one off steel hull, very unique design but I don't know anything more about it. Very lightly equipped, wind vane, few electronics, no radar or reefer. Less problematic than their dinghy in the Bahamas, for me, would be their draft; 6'
I saw the bright orange Pudgy on the foredeck. I'd bet it will rarely be up there as one of a Pudgys better qualities is towing. I wish I had asked them more about it, hopefully she'll write about it in a blog.
As far as how they'll use it, they've done this trip before, at least once, so I doubt they'll be surprised at the limits of the Pudgy. I wouldn't be surprised if they have an electric or small outboard(I didn't see one on the rail though).