I assume this is a US market Pontiac/not Canadian? You can do a Chevy or wahatever else you want but you'll have to find an adapter or fabricate side engine mounts. Pontiac used the front mount up to 59, so any engine 55-59 should be a bolt in.
I mounted a 60 cover, standard coolings first year and steel cover to a 66 389. The 60 cover to be mated up and using the bracket and front mount to about any year/set up Pontiac to take care of the front mount. Than some rear side mounts would still need to be made. Fabricating side mounts would be easier for a newer side mount Pontiac engine. Swapping out for a 350 would be out of the question for me. Whats wrong with the 316?
350 chevys in old 50's hot rods make me yawn!! keep the 316! love the stance of your wagon ,what did you do to get her down in the dirt?
why struggle with oddball engines ---if it is in good shape use and enjoy---if not sbc for all the well known reasons
I have Mule Farmer's old 56 wagon, and yes the 316 is a good motor, 220 horse is enough to get the wagon moving in a hurry when tuned right. I now have it with a modern 500 cfm Edelbrock 4 barrel on a tapered Speedway motors adapter to an original small bore four barrel intake. Its getting tired, a bit smoky through the breathers and could use a rebuild but even so it is still is a stump puller. I have read that early on V8 Pontiacs had problems with bad ring metal and they would break, I am probably going to pull it apart and see if that is true in my case, could just use an old fashioned ring job. Stock auto tranny is pretty tough and takes a beating pretty good. If yours it isn't wasted I would try to work with it. A new 350/350 would cost as much as a little investment in the 316 which BTW is all forged internals crank, rods and pistons; try to get that in a 350 for less than $5K