If our main organizing principle at the top level is to put the coins as close as possible to the current nation (and as long as there is no compelling reason against), we keep Hawaii where it is.
And we put Puerto Rico as a sub-issuer under the USA.
If the more important organizing principle is the status at the time of issuing the coins, then we could follow Krause that has them both as top-level issuers (but we are not always following Krause).
To me, we are mostly organizing French-Feudal, German States, and Italian States along the lines of the current national boundaries, regardless of previous history. So it would be consistent to have both of these places under the U.S.