I put a 292 in my "53 2 ton...It wasn't that bad, since I had the whole front end off. Welding the engine mounts in the right place was probably the hardest part. (And that wasn't that bad.)
Not much room in the front. Had to modify a pulley on the H2O pump and I got an electric fan that works great. Had to add a port in the top of the radiator for the sensor...
I changed everything to 12v with the engine swap, and a 1 wire alternator. I used a painless wiring harness for that- there were a few things I had to modify on the harness, but wire locations worked out well.
Had to stay with the old style transmission, since the new style would not fit. It's tight! The transmission cover had to be modified to fit, too.
Went with cast iron 2pc headers. Can send some pics if you want or answer specific questions....Renee