I'd advise that the first line in your plan needs to be for a hydraulic roller lifter conversion if you keep the 327. IMO if you choose to stick with a flat tappet cam you're just throwing your money away, or at best gambling when it will fail. There's simply too much evidence out there to chance investing in new parts and then staying flat tappet.
A good article on budget builds using OEM parts here - Chevy Small Block - Car Craft Magazine