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Do NOT put on larger primary headers. That will kill the lowend.
I would also not use the 4.88 gears or the tunnelram. The tunnelram would probably run good, but that's not the "look" you're after. Like you mentioned, I'm also not a fan of slow "racecars".

The exhaust will benefit from a crossover...X pipe makes more power than an H, if you don't mind the sound of an X pipe. Either one will be better than true duals.

I don't argue that a straight through muffler flows better than a flowmaster, but on this combo I don't think they'll make much difference. I ran an old pair of 3" 2 chamber flowmasters on my car when it was running mid 11s...made no difference w/ or w/o them.
If your flowmasters are the bigger 3 chambers, then scrap them and get some straight through mufflers like a Dynomax ultraflow or Hooker max flow.

The Holley SD is a VERY good manifold...I'd stick w/ it.
A properly tuned bigger carb will definitely help. 440's love cfm...put an 830, 850, or even a 950 double pumper on it.

I'd keep the cam you have.

You could always throw some .020" thick steel shim head gaskets on it to gain some compression quickly and easily. Cheap too. Of course it wouldn't cost much to have another .020" or .030" shaved off the heads while you have them off.

It would probably like a looser converter too. You can have your current converter loosened up by any of the good converter companies.

In my experience, the electric water pump will be worth nearly a whole tenth in the 1/4 by itself.
On my car, I dropped a little over a tenth by eliminating the big clutch fan...still had the mechanical water pump.
Dropped almost another tenth w/ an electric water pump.
If you get one of the moroso water pump drive kits, you can switch to it at the track...just swap to a shorter belt and change the pulley at the track. The moroso water pump drive will not keep cool on the street.

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Just to touch on this.

My Flowmasters are the 2 Chambers as I recall. It was years ago that I purchased them but I'm 95% certain of this.

I already have the steel head gaskets. I am not entirely opposed to cutting my current heads though. Just haven't committed yet.

I will without a doubt try the 850 once more. Not necessarily the same 850 though.

The Street Dominator will be going back on. It was the better performing intake in this application.

I also will be installing the electric water pump (Direct Drive). If nothing else is gained but ease of cool down in between runs, it will still be worth it.

As far as converter replacement, I've got mixed feelings. I would hate to lose street driveability. It's marginally obnoxious now with the 3500 stall and 4:56 gears.

4:88's are on the fence still. Once I get my motor to rev past 6000 without slowing down it may seem more tempting. I was pretty interested in a low gear set for the 727 as an alternative as Cab mentioned, then I priced them out.

Anyhow, Thanks again everyone! I really appreciate the help and input you offer.