Well, I don't have any experience with a 216, a t5, or a 49 chevy, so don't take my opinion as fact. I believe t5s have been placed behind 216 motors. I would not think a transmission and rear end swap would give you a whole lot with a 216 power plant. However if you were to change the 216 to a 235 or even better 261 at the same time, I believe the swap would be much more worthwhile. I would continue driving the truck like it is and start gathering pieces.