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I personally believe that you should go with a 270 grain Gold Dot or a 300 grain cast core bullet. Punch a nice big hole. That is what kills them when you are using a handgun. Even the heaviest .44 loads impart nowhere near the energy of a rifle. I stay away from JHP's myself- but that is probably because of the tales I have heard of wild boar not being stopped by a hit in the shoulder (because of their "armor"). 240 grain JHP's may be fine for "thin-skinned" game, but I would still prefer a 240 JSP like the Winchesters you have.
I would not take a shot unless it was a perfect standing broadside shot from a good rest if it was much past 50 yards. I use open sights on a 4" revolver and consider 35-50 yards to be my maximum confidence range.
Your rig will do fine at 100 yards from a bench at the range, of course.
Just a few thoughts.
Oh yeah, those hot 180 grain JHP's are great on jack rabbits and milk jugs filled with water.
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