Good plan, highly viable. Some characters end up hardly using their game-system skills.
Think about what sort of thing you mean by “bard” though… in larp, people often use the word to mean any musician or singer, though the real-world-historical kind of bard isn’t much of a thing in Empire, at least in most nations (though maybe the Wintermark skop comes close to the Icelandic bard)… but all Empire nations have their musicians, storytellers and suchlike entertainers, and good ones find themselves appreciated and rewarded by Empire characters (whose players enjoy the entertainment as well, after all).
Just as an example:
I can vouch for that… though the Houdagen are far from the only ones, of course.
My League character is the “theatre-troupe magician” archetype, but first and foremost he’s a violinist, and he has built up a good IC reputation as a violinist, through a mixture of self-promotion and playing well. (He does sing occasionally, but it’s not serious.)
There are plenty of different kinds of settings for music: not just in someone’s camp or tavern for tips, not just busking on the street, but also in proper concerts, or being paid to supply music for dancing (or dancing lessons), or to accompany a play, or as part of a ritual: my character often uses Silutaris’s “music of the spheres” approach when casting a ritual solo (but when working with others it’s more often dramaturgy, as is typical for the League).
Um… good enough that people will enjoy it! But since you’re “a classically trained musician” I take it that you play at least one instrument well? So you don’t necessarily need to sing anyway. What do you play?
Well, my character found some at the first event, and over the time since then they’ve come and gone but there have always been some. Really the limiting factor for me has been my time and enthusiasm rather than people, because the top priority at each event has always been the troupe performing at least one play. Sometimes I’ve done some organising/planning with other musicians leading up to an event, sending emails to represent in-character letters, and sharing copies of music, so that at the event we can get away with just a little bit of rehearsing. Once we did some rehearsing for a violin duo on the Friday before time-in.