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I can answer a couple of your questions but not all:
A caliber converstion includes a shell plate, three "buttons" and the powder die.
Yes you would use the .40 shell plate and buttons for .357, but you would need a different powder die.
The 9X25 Dillon is a bottlenecked cartridge based on the 10mm case, similar to the .357 SIG concept which is based on the .40.
As the AT 500 does not come with an automatic powder measure, the "package deal" supplies you with a scale and some of the other extras you need to run the press. You will need to buy caliber conversions seperately.
I suppose the short answer to all you questions would have been to tell you to call Dillon. They are extremely friendly to the point of ridiculousness. Call them, they'll help you anyway they can, really good people.
800-223-4570
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