It'll be a great day for amateur golf when people stop conflating the allocation of handicap strokes on the scorecard to hole difficulty.
Talamore in Philadelphia has the first stroke hole as the opener. But it's not the most difficult hole on that golf course. I don't agree with the OP that the first at Lake Jovita South (which I've played once) is the most difficult hole NOR do I agree that the first at Toftrees (which I've played many times) is the most difficult hole at Toftrees.
Despite their stroke allocations.
The Jeffersonville selection is an interesting one, and like many of these conversations, perhaps says more about the player than the hole. There's a line to take from the appropriate tee that cuts off significant distance. It's never been the most difficult hole there to me (8, 11, 13, 17 are all better candidates) though a golfer can make it difficult.
And that's sort of the crux, to me, of this conversation. Stroke allocation is as much about where the bogey golfer needs TWO strokes against the scratch, if not more, than where the 1-handicap needs a stroke against the scratch. The first situation likely involves a penalty stroke while the second situation likely involves a difficult putting green.
Difficulty tends to boil down to two things: Possibility of a HUGE number v. difficulty in making par or better.
Let's call that the "Tobacco Road Assumption."
Now that I've stalled for more than enough words I'll nominate my candidate: