First Time Builder- What Can I Expect?

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So I picked up a 65 with a a little 289 in it. I plan on starting the engine rebuild here soon and was hoping you experienced guys can tell me what type of horsepower I could realistically obtain. I plan on stroking it to 347 and upgrading to a 4brl carb. I'm also a huge fan of boost and was thinking about getting a Paxton supercharger to keep everything under the stock hood. Without the cost of the charger ($4300), what do you think the grand total would be? Horsepower and torque? Is about 500 at the flywheel a crazy number or what? I really have no idea what to expect out of this build. What are your guy's recommendations?
Motor aside, I would expect lots of surprises. If you start tearing these cars down you will undoubtedly enter the cycle of....'well I've got it this far apart, might as well do that too'. It's only money though. Surprising how many ways you can fool your kids with Kraft dinner ;^). Good luck.