It's all very subjective. I find the 39 PB aesthetically displeasing; it is not, to my eyes, an attractive photo of The Yankee Clipper, what with the eyebrows and the teeth.
For my representative Joe D card I chose the Zeenut PCL, which is his first-ever card appearance; I much prefer the batting pose, because of his exploits on that side of the game. I also like the piece's rarity (I believe PSA has only graded 8 with or without the coupon, for example).
For a burst of color, I like the 41PB. It's also the card associated with the 56 Game streak-- and that's a critical piece of both baseball and card history right there. It should be noted that none of the early Joe D cards-- the Zeenut, V300, V355, etc.-- have the color the 41 PB does. I would go with the 41PB from your options list. I also think the 41PB is the most popular and "get-able," since the Zeenut, V300, and V355 WWG are so scarce and also expensive. But again this is subjective and debatable. There's a nice write-up on the 41PB in this link:
Joe D 41PB in PSA's Top 20 Sportscard List
I am also a huge fan of the V300 and the V355, the latter of which some consider his rookie in terms of first Yankee card appearance. I think the V355 has serious charm. Kind of a thuggish mugshot photo and the cool nickname "deadpan Joe" on the back.
Ultimately, as someone said so well above-- go with your taste and you won't go wrong.