Any bearing that fits your axel, most trucks are normal and most bearings are the same diameter so don't worry about it. So yeah any bearing.
But I've built a few boards, you can look in my profile to see the pictures. You could probably go with the classic pintail shape or a variation of it. Don't go for anything too radical yet, it's not as easy to get sharp beds with baltic birch, which is the wood you want. You're looking for real wood (no filler), 1/8" or maybe 1/4" if you can't get the 1/8" . If you want a more radical bend, you'll probably need 1/16" or thinner maple.
Press-wise, your best bet it the dimm or positive/negative style press from that video. It's easy to make, just take your time on the foam molds.
Fiberglass only helps on the bottom and top, it really only has tensile strength. Glassing doesn't need to be done on both sides to help, you can do only one (as far as I know) But it only helps on the outside since only those layers experience shearing and are exposed to tension when the board flexes/is weighted. But if you're just starting just don't worry about glass yet.
And like whoever said above, I've been doing 4 layers of 1/8" baltic birch with varying concaves too. I've got one with a bit less than 1/2" concave and a 29" wheelbase that flexes a bit, and one with 5/8" concave that has almost no flex. No glass on either.
And the shape does influence ride. You're gonna wanna consider torsional rigidity too, a more rigid deck should be more responsive. I think a less rigid deck has some use for sliding? Something about the back trucks... Not sure on that one. Wheelbite is something else to consider. You can do cutouts or wheel wells, just try to keep the area near the trucks a decent size. What I've done was draw my shape, generally, then transfer that to the wood. Then I'll loosen the trucks a lot (they're not attached yet), and bend them to see where the wheels will hit and let that dictate the final position of wells or cutouts.
Feel free to keep asking questions, I feel like all of that was disorganized.
