Yes it would be really cool

Just how would they do that? They already established John Wesley Shipp and Amanda Pays as different characters in-universe.

Actually Amanda Pays, Alex Desert, Mark Hamil and Vito D'Ambrosio are all playing the same characters they played in The Flash(although smaller roles) : Tina Macgee, Julio Mendeze, The Trickster and Tony Bellows.

It's clearly implying the original series takes place in an Alternative Earth, Similar to Earth 3 where everything happened 30 years earlier, so it's not that much of a stretch.

John Wesley Shipp Is the only one playing a different character, but that was sorted out when he started playing Jay Garrick, In the original series Jay was his older brothers name, so even that is implying that somewhere out there his parents had two children, the first born was called Jay and he is called Barry.