Rowena's (Jean Louisa Kelly's) voice is clearly exceptional. It fact the actress has performed on Broadway. Someone with a voice like that, combined with extremely good looks is a can't miss star. I believe its suggested by Mr Holland that she was destined for greatness. If he didn't believe this, he wouldn't have encouraged her, instead, he hooks her up with a place to stay and a contact in the business.
For me, they bigger question is why didn't she attend the ceremony? Its quite possible that she was too busy to attend. But my belief is that she had fallen in love with Mr Holland, and that it probably took her a long time to get over him. Seeing him again would be too difficult.
I believe Rowena was a muse to Mr Holland in their brief time together. Within the muse/artist relationship there are often elements of seduction/temptation. As you suggest, she also appears at a time in his life where he may be having a "midlife crisis". Mr Holland was, in the end, a moral and ethical man, who made the right decision for all concerned.
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