Well, lets take a real hard look here,,,,having done the nailhead swap in the past, to me , it was a fairly easy swap , if you can gather up the correct parts.... that is the only real problem with going the nailhead route,,,,but if I were going to build a nailhead to go in there , it would be a 425.... with a switch pitch th400.... that way i would have a strong running , reliable, engine /trans combo that would stay with the best of them....and i would not have to do a bunch of expensive mods to make it live.....with the forged steel crank and forged steel rods and the good oil system and good cooling system it is very dependable.... + a switch pitch th4 will put massive amounts of power to the ground.... and with a gear ratio like 3.08 or 3.42 it will get reasonable gas mileage....my personal GS is set up with a 410 block, good hot cam, and my ''Doc dual plane'' intake mod and a holley 1050 cfm three barrel carb.... port matched exhaust manifolds and 2 1/4 pipes and turbo mufflers.... and my red neck ram air , air cleaner assembly....
You could adapt all the modern stuff to the 300 but that would be a expensive can of worms.... [ efi ] ect.....
If you change to a nail you will have to change the motor mounts/frame pads/starter/exhaust manifolds/rear crossmember/ exhaust pipes/ air cleaner assembly..... and you will have to change those exact same things to install a 400/430/455...... but the massive amounts of torq those engines will reliably move the car....
I consider the nailhead to be more reliable than the BBB,,,, no oil system mods need to be made, the head have 5 bolts per cyl... not 4......forged steel rods, crank ect.... nails have 2 things you have to watch for.... the harmonic balancer will very rarely crack in the keyway in the hub.... and with high mileage the factory cast pistons can fail.....they get brittle and start coming apart.... but in 50 years of messing with nailheads I can count on one hand the engines that i have found that have done those things....
as for looks,, no engine looks as good as a nailhead dressed out....period....
but nailhead or big block, either one , if done to stock specs will do fine in that car....
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