your using it as a daily driver so i dont understand your reasoning in having something 400hp in your car. i'd stick w/ the 327 if its in good shape, put some nice pistons, heads, intake and a nice carb on their and your fine. if you want that hot rod sound also put a semi-mild cam in it, some where in the mid .3's. i believe comp cams has blueprint muscle car cams, exactly like the ones they used to put in cars during the muscle car era. jegs has those cams. if you go too crazy you wont be able to drive the car on the street, so keep it moderate.
as for trans and rear gears, personally i'd go for a well made 700-r4, but thats only my opinion. the overdrive is nice, and it has a low first gear to get going quick, combine that w/ 3.73 gears and you'll be good, in my opinion at least.