Pommels in the fishtail style, that of "the Regent" and some Estocs among others, are very mid to late 1400 - but when did these first appear? Are any fishtail-pommels ever seen in the late 1300? The XV sword of Estore Visconti looks like the shape of things to come to me, but it would be nice to know the very earliest form of the fishtail.

Let me rephrase; can anyone think of ANY excuse to use a Type XVIII with a transitional armour? Have my eye on a sword (Pavel Mocs Italy Estoc) but as far as ive been told it does not fully match my fighting-armour.

I haven't had time to look through my books to fully address the pommel question. Our article on Oakeshott states this for the Type V pommel, though:

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The type seems to have been confined to Northwestern Europe and also seems to have been fairly uncommon if not exactly rare. It seems to have been in use for most of the 15th century.

The Visconti sword's pommel is really more a scent-stopper. I'm not sure it's very related to a fishtail.

As for Type XVIII's, there are at least two that Oakeshott dated to the last half of the 14th century. One is the disputed sword of Edward III. The other is in the Met and some have dated it later (1400-1450).

It might not be unheard of for a Type XVIII to exist in the late 14th century, but one with a fishtail pommel (so clearly identified with a later period) would be a stretch. From our Spotlight article on Type XVIII:

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According to Oakeshott, Type XVIII and its subtypes were "the most widely used swords between c. 1410 and 1510 all over Europe".

Diamond cross-section swords are depicted in medieval art in the late 13th century, but they are really closer to Type XV than XVIII.