Engine cooling has never been a problem with my 964s (all normally aspirated) in all those years; neither on the road nor on track. Not even on tracks like the old Hockenheim on a real hot day. When the 964 was raced in the Carrera Cup (rules were very strictly controlled) some racers tried to keep the engine lid a tad more open - not for cooling, but for more fresh air.
A 964 is pretty much bulletproof as it is. Brakes can be an issue in case you want to track it, especially the two-pot rears of the early C2.
A lightweight project is good fun (and helpful), but drilling all these holes won´t probably help, it seems to have a more or less psychological effect. I have seen a car with drilled doorhandles - leaving your watch at home saves a lot more weight I guess. But hey, nothing wrong with living your personal dreams.