I don't think you can update this show to a more modern era -- i don't think any modern musical with this premise/plot (the draft part notwithstanding) would be written with these songs, re-arranged or not. Bye Bye Bye is wonderfully of its time, and I don't think there's any point or profit to trying to pass of these songs as if they were written today, or not written specifically for a story and characters and musical style and tone and sense of comedy that is in the late 1950s.
