When you create an order on IB, you can set a “time in force” date. The order will only be activated after that date has passed. This way, you can open TWS just once and add orders for the next year so you don’t have to log in again as long as you have sufficient funds. The orders will show as pending on the TWS.
I actually create these recurring orders with a Python script, but it should be quick enough to create them manually too.