Hi all! Much as taxidermy fascinates me I don't think I ever foresaw that I'd be signing up for a forum

But this method has spread pretty far and you guys seem to be the most knowledgeable about it (and way nicer than most forums I've run across lately), and I had a few questions before I invested the time in using it.
I have some small mostly-columnar sculptures, about two inches high and about an inch across. They have some curves in them, a little less than the degree you'd see in a coke bottle. There is a fat part near the top and then a slightly thinner "neck" underneath. It's not a lot thinner--just very slightly dips in, as if it had been lightly compressed with a finger. My question is this:
If I mold them so that the base of the sculpture is the opening of the mold, would they successfully release from the mold? Is it flexible enough, or would the fattest parts get caught in the "neck" of the mold and refuse to release? It's hard for me to tell from the pictures etc. whether this mold would suit my purposes or if (sigh) I am going to have to make a two-piece mold and deal with the flashing and associated mess

Grrr undercuts!
I need about... oh... fifty of them? From around five original sculpts. Would the mold hold up to that many casts--around ten per mold? I'll be casting in clear resin.
If worse comes to absolute worst, I can make the mold individually each time and break it for each cast, but I'll have to raise my end prices considerably and that's also kind of a pain

Thank you in advance for y'all's help!