On Caslon, the reason you didn't find a "straight answer" is because there isn't one universal answer. If you print sloppily inked letterpress on soft, damp paper using foundry type that closely approximates Caslon's, you will get a result that looks like typical eighteenth-century printing. If you use a different technology, you have to make choices about which qualities you will emulate. Founder's Caslon is the closest digital design to the outlines of Caslon's own foundry type, but it's "cleaner" than the normal eighteenth-century ink spread or the texture of the paper, both of which Caslon may have allowed for in designing his type. Is that "real" or not? That depends on you.

As for coin design, I don't know what your question is. The letter and number punches formerly used in making coin dies were certainly similar in nature to the punches used in making type matrices - I expect it would be interesting to know whether they were ever made by the same people. Medals are different, after the invention of the Janvier lathe - the lettering is often modeled rather than cut.