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I think pp. 46-51 of Benedict XVI’s book Jesus of Nazareth: the Infancy Narratives addresses some of this issue.
P. 49 sums up four hypotheses of interpretation of the passage, then concludes none of them quite fit.
In Benedict’s exegesis, though, he translates ‘almah’ as ‘virgin’ and perhaps it’s not difficult to see that a ‘young woman’ could be that. Perhaps in fact with the hindsight of seeing that God pulled off the impossible and that the Virgin Mary did conceive and bear a son even Isaiah would testify that that word is an excellent translation!
At any rate, Matthew’s choice of ‘virgin’ is not a proof text so much as a celebration of what had become reality. It is ratified by Joseph’s whole experience in Mt. 1 and with Luke’s Gospel’s announcement of the Annunciation.
Finally, I really liked Benedict XVI’s summary on p.50 into 51-
that the sign was not addressed merely to Ahaz or even to Israel, but to humanity (through Israel, with Mary and Joseph as the ‘root Israel’:
“The prophets prediction is like a miraculously formed keyhole into which the key of Christ fits perfectly.” (quoting Marius Reiser from Bibelkritik, p. 328) So, again, it’s not a ‘proof text’ but a source of amazement for those who believe.
I’m not an expert but you can see I’ve been doing a little thinking on it.
To conclude, here is a page on a website about Our Lady of the Sign: (the author uses Isaiah’s ‘young woman’ without batting an eyelash!)
Hope this helps.