i know there is no correct answer for everyone but…
what press number would you go for
if you are trying out a new shape?
a two or a three seems like it would make sense
and for the real sickos
did you try every mold to find your favorite?
I have ended up with every number in a few sizes, but I have definitely had more than a few of each stamp in the 8.38 shape, with varying degrees of comfort.
Besides the fact that I have had I stamps, more than one, all with teal tops, that were more mellow than any IV stamp, or that some just seem to be so flat they initially seem like they might be too flat, but were ok, most of the I, II, III and IV stamp boards have fit fairly well into the general mold of I being steepest and IV being flattest, in overall comparison.
More than anything I think it just comes down to what you prefer, as some people do prefer the more mellow boards and others prefer the steeper boards, so it just sucks when I hear people on here say their board is too this or that. In person it is a lot easier to sort out, as I have swapped out boards from people in the past to something they prefer, but that is another story.
The 8.25 board has always seemed to be steeper in any case, compared to the 8.38 board, with the blue eagle 8.5 being almost in between those two on average, even though I think it was said by someone in the know that they are all made on the same presses.
The Anchor shape 9.02" board I got in a IV and it is very easy to skate. One orange eagle 9 x 33" I set up is a I stamp and it skates fine too, whereas a few other shapes including a Beach Bummer 10", a Horse Pill 10" deck and a couple of others I got are also a I and they are a bit too up there in concave for my liking.
I put it down to the shorter boards that are steeper are harder for me to get used to, whereas a longer wheelbase board is easier to get used to in a steeper mold, or at least that seems to be the case for me. I would say that the longer wheelbase boards are made in the bigger mold, so it is not just how the board is cut, but the fact that it is a bigger mold that makes it work more for me.
* Sorry that might be a bit too long for a simple reply.