If you pull some valves out and post some pictures it would be easier to tell you how to proceed porting. Also...I don't know if you've bought a torque converter yet, but I'd recommend a 9 1/2. They are tight and you can cruise on the street just fine, Imo your 383 combo is going to respond to more stall then 2900. Ptc or dynamic...good choices.
Porting my concern would be going straight in the bowl deep with 2.14s. It likely will get thin as you approach the radius. The short side I don't think you will have any trouble just blending it. But, I believe the exhaust are where guys tend to grind to much on 516s and hit a water jacket, they seem to lack cfm on the exhaust even after port work (compared to the later heads).