Doing a Pontiac motor would be cool too, since you don't seem to be looking for brand uniformity. The 307 mounts are easily available, but you've already got the Pontiac mounts... It's a good problem to have, lots of options. I'm not sure, but fan shroud may be something else to consider, since you already have a Pontiac motor. I believe there is a difference in mount location for Pontiac motors, it may be around '68-'70 where the change happened, if you went Pontiac you'd want to have a block with the same mount provisions as the 301.
As for differences, they're both obviously completely different motors. They're both reliable and there are parts available, not like for Chevy, but you don't need a ton of parts, just the right ones. I know Olds motors aren't considered the best for extended high-RPM usage, long stroke and slow oil drainback, but then there are guys with Olds 455s in their boats, it's not an insurmountable problem. Plus, a 455 doesn't NEED to rev that high, it makes it's power down low and lazy, that's why they're so much fun. I've HEARD that Pontiac 455s have some issues related to stroke length and geometry, but I don't think it's a deal-breaker. If I had a Grand Prix, I wouldn't hesitate to put a Pontiac 455 in it, but I'm a brand uniformity kind of guy.
Once you make your final decision on which way to go, it will be easier to come up with a plan. My advice would be to get a running motor/trans combo with all the accessories and brackets, that way you don't have to hunt around for everything. It's mostly all available, but some of it is harder to find and it's so much easier when you have it already. I'm excited to see what you end up doing.