If the oil and water galleys match up, and it bolts to the block fine you should be good. You will probably get a very high compression ratio from this set up.. I had a small block .305 and I switched out the stock 64cc heads for a pair of 49cc heads I got a much higher compression and gain in hp. You really need to analyze the heads and block in question and surf the forums for a better answer.
Yes, and well.
yes
yes the heads will bolt right on but if you are putting a 305 in there the flywheel is different in the sense that the 327 has a small hole where the flywheel meets the crank (you need the starter for the 305)
The heads will fit the block, but the vortec intake manifold will not bolt to the old style heads.
The 305 shares stroke dimensions with the 350, so if you put a 327 crank in a 305, you'd have a de-stroked 305 with almost no compression. Displacement would be around 287 cid.
yes just get head gaskets for the 350 not the 327
No. You would need to bore the block to 4 inches, which is too much for a 305.
Into the heads only.
Yes you can.
Yes their the same block....
A 350 block with a 327 crank is called a 327. Bore it 60 over and it becomes a 337. Don't know what pop up heads are. Never heard of that.
Because of the 305's small bore, you're pretty limited. Large valve heads (2.02/1.60) won't work on a 305 because the valves will hit the block itself. If it's an older 305, your best bet would be the old power pack 283 heads. They flow better than the older 305 heads. Now, if it's a vortec engine, you probably won't do much better than what it had stock. If you are really trying to go fast, the best thing you can do is junk the 305 and replace it with a 350 or a 327.