I recently bought a 69 Chevy p/u that somebody stuck a Pontiac 400 in. The transmission is out and it's going to cost a lot to fix. I'm thinking it may be better to just replace it all with a 5.7 or 5.3. I'm open to suggestions but remember... I'm a cheapskate.
I'd bet fixing the current trans is going to be a lot cheaper than replacing the engine/trans with a Chevy V8. Lots of people are going with the 5.3/4L60 swap in these trucks but there is a bit of wiring and plumbing involved along with a donor wiring harness and computer. 5.7s are getting hard to find in decent shape.