There would be no significant difference between applying stucco to your house and any new home sheeted with plywood. Architectural details would be added using wood or foam forms, followed by a moisture barrier and lath that would be applied over the T-111. Applying the several layers of scratch and finish coats is not something most DIYers are capable of pulling off. But there is no fundamental difference in the way your home is constructed in terms of framing and materials and it can be done. Get references and bids, and it might be a good idea to get an architect to help design a compatible, updated looking exterior.