Your car sounds an awful lot like mine!
$2K will get you into a 331 with quality parts.
The decision for me was that I want more cubes, but am on a budget. Someone mentioned the 347 rod ratio being less than optimal, and that is true. (331 has the same issue, just not quite as bad.) It can cause accelerated wear that impacts durability. I am not one of those guys who pulls the engine every winter, so I went with the lesser of the potential issues.
I think the parts you have will NOT get you the 400 number at the flywheel with a 306. You will be closer with the 331. And MAYBE get there with the 347, but you may pay a penalty in durability. If you are putting 3000 or more miles on the car per year, or open-tracking on a regular basis, I think the 347 will need freshening far sooner than you would like.
With that I have a set of old Edelbrock Performer RPM's, a 220 / 224 Comp roller, and an Explorer upper & lower. I'm planning an Aviaid road race pan and all the other goodies (similar to your list) to build the engine complete. With my 60cc chambers, I am just under 10:1. I expect to make about 375-390 on pump premium after a tune.
Good luck!!