Caveat: I ain't no sort of naval architect. I may be all wet here. However....
From what I've read, I'd agree that a sprit-boomed leg-o-mutton sail like those on the Jimmy Skiffs can be difficult to reef, and impossible if the sails are laced to the masts rather than hoisted, as I believe is the case with the Jimmy Skiffs. Working boats using this rig generally had at least two different rigs, maybe "winter" with a smaller sail and "summer" with a larger sail, and the waterman would pick whichever one he thought would be best when heading out for a day's work. If the wind got to be too much, he'd strike the rig and row. Those were tough men and women in those days, and they tended to die young, anyway.
I couldn't find a sail plan of a gunter rigged Skerry for comparison, but, looking at the sail plans for the sprit rigged Skerry, the Jimmy Skiff II, and the gunter rigged Passagemaker, it looks as if they all place the center of the sail area pretty much right over their daggerboards. IF the distance between the Jimmy Skiff II mast and daggerboard is about the same as with the Passagemaker with the gunter rig (the mast location with the lug is different), you MIGHT get away with it.
If you're clever with Photoshop, Visio, or some other tool which allows you to measure images, you might be able to check this by using known dimensions to get the two drawings into the same scale for comparison. Mind you, the Jimmy Skiffs' daggerboards have consiterably more "rake" than the Skerry or Passagemaker, which may matter here.
I say this with a great deal of caution. This whole business of establishing the "lead" (the distance of the center of the sail area ahead of the center of the lateral immersed plane area of the hull in plan view) in boat design is a mighty tricky thing, and even experienced naval architects sometimes get surprised. The idea is to produce a result which gives the boat a wee bit of weather helm in most conditions, and never a lee helm, which is more complicated than just comparing the lateral areas in plan view. Hull shape enters into it, as much depends on what happens as the boat heels, etc. Also, the nature of sail rig plays a role, as well, e.g., tall vs. short, length of booms relative to boat length, etc. However, with small, light displacement, shallow-bodied boats like these, maybe the location of the sail area relative to the daggerboard/centerboard/leeboards is the the main thing. But, what do I know? I just get this stuff from reading.
...or, you could call or write John Harris and ask his opinion. He loves to hear from builders and surely knows more about it than I do!
.....Michael