I am not a shim gasket fan, Frank is right that more squish usually helps, need to see where you are and where you'll end up though, but the downside is every stocker that comes through here is crooked and wavy, sometimes severe. If you add surfaces that aren't freshly machined, the shim combo can result in a poor seal compared to a composition gasket (although a standard head gasket can fail too in the same situation). My advice, old parts, standard head gasket. Freshly and accurately machined, let it rip.
I am not a Performer 390 fan either, performance isn't much different than stock, but the weight sure makes it easier to drop on! I'd be hard pressed to not use it if it's the only option. Better power makers and how much, depends on end use of the engine, gears, tranny, vehicle, etc.
The 735 is a good carb and the fact Drew went through it makes it more likely to work well than any of your other choices, nd is not too big.
As far as general advice. 1 - headers and good duals with a cross over, 2 - recurve the distributor to match use, fuel and engine details, 3 - gear for use and shift improver kit for an automatic, 4 - improved 4 barrel carb and intake (you have a good start). Those 4 things are the low hanging fruit that make a car fun to drive and reliable, after that you go inside.