Richard,
How about I jump in on this, and with that, I hope I'm not butting in. But let's see if it helps "Orange County" some.
I copied your questions and have answered them for my project--a 327 build-up. Promise...I won't have my feeling hurt if you balk at some of my ideas. Just hope you and others will feel open to solidly critique it.

How much money will you spend? As much as necessary.

Is there a time frame in which this project must be completed? No, I've had this car since '79! So while I'm just starting, I've learned to be patient (LOTS of project cars for my son...Now it's my turn!)

What is the weight of the car? Should come in--when completed--at around 3400 lbs. I'd think.

Will the motor have to pass emissions? Nope.

Does the car have power brakes? Nope--will have 4 whl discs though.

Will you do the work yourself? An awful lot of it, yes.

Do you have the proper tools? Yes.

Are you hung-up on the 327 or would you be just as willing to build a 350 or a 383? I've GOT to do this motor. It's all about always wanting to build one--since '68 when I had my other '55 and had a screaming little 292. I have this small journal 327 available and am determined to build a stout motor out of it--just for grins and to capture some of "the good old days".

Do you have access to a good automotive machine shop? Yes a very reliable one who does alot of "old iron performance stuff".

What transmission will be used? The Keisler Tremec 6-spd (Ratios: 2.97, 2.07, 1.43, 1.0, 0.80, 0.62)

What rear end? Currie's 9" w/disc brakes
What gears? 4.33

What % will be mild-mannered street driving and what % of the time will you be down on the loud pedal? I'll be using this for limited (1-2 times a month) cruising but will have to run it once at the strip--just to see.

I'm planning on the following build-up:
Bore .040 over -- it's already .030 with all the necessary line boring and decking, magnaflux etc.
Eagle Crank Stock Rods TRW pistons .125 dome Dart Pro 1 64cc Alum. heads (2.05 / 1.60's with 1.55 dual springs) Isky roller rockers Isky Z-70 cam .548 .264 adv. dur. 108 degree centerline Solid lifter ('cause I like the noise and don't mind the maintenance!) Edelbrock 2x4 intake (I know it doesn't match the build-up, but I want THAT look, you know?) MSD ignition Hedman headers with a CCI 2 1/2" exhaust system thru Turbo's or Flowmaster's..not sure.
Yes, I'm aware it's impractical with todays gas and plan on 1/2 & 1/2 92 octane & Union 76 race gas.
I've had many friends tell me "your whacked!" "Why a 327??? You could build a monster 383 for the same money!" Answer: 'cause I want to and I can! I really do want comments and questions. I've waited a lOONNNNNG time for this and I want to do it right--while still having "The sound" and "The Look". So dive in and maybe it'll give Orange County some ideas to use or avoid. Thanks.