Hey jls!
I have had fairly good success with both basket stamping and tooling holding up during the molding process if I am willing to give up a whole lot of forming and boning on the front. I tool or stamp the front panel of the holster, whether a separate piece for a pancake and let the leather dry, or the front half of a wrapped style like an Askins or a western style which I fold into the general shape and then let the leather dry. I then do whatever sewing I have to do and get ready to re-moisten to form. Notice I said re-moisten and not SOAK! On a pancake, I wet the rear piece real well and then the INSIDE ( or grain side )of the front piece a little. With the wrapped style, I dampen the non-tooled part fairly well and then less moisture on the tooled part.
It's kind of a feel you will develop after you've done a couple. You don't want the inside (flesh side) of the tooled portion so damp that the front side (grain side) darkens from the water. Let the whole thing case until it starts to all go back to it's original color and then insert the firearm and start forming. I form and bone the back and non-tooled parts fairly well. If I need to form the tooled portion a little, I try and form it in a little with the tool I made the impressions with (backgrounder, bargrounder, thumbprint, whatever). I like to put concealment holsters on my belt in the carry position before I insert the gun. That way the holster is formed to my body and to the firearm all in one shot. Once the holster has been on the belt for a little while, you can take it off and bone the back of it. You'll see that the belt slots are formed and slightly burnished.
Hope this helps.
Mike