I suppose I could generate the activity log for the trailing 365 days (it won't go longer than that) and then match it up with my current positions and by process of elimination determine that if my purchase isn't on the activity log it must be long term by now.
Most convenient? Sign up for the automatic notification IB provides. Less convenient, download the portfolio with a flex query and sort by date purchased. Also I think there is a "lot" buy sell, feature so you can specify which are bought and sold specifically, and can manage it down to the lots.