It's nothing drastic. My old 383 had a little groud off the bottom of the cylinders, and a little off the oil pan rails. Just about 1/4 of an inch to clear the rod bolts.
If you are planning on selling the car you have to weigh the cost of a stroker, with the "ohhh ahhh" factor selling a S/C, nitrous, 383 will get you. I think you'd be able to re-coup the couple hundred bucks it took to make it a stroker.
Overbore. Here's my take, from a BDR perspective. Mic the cylinders and if they're within .008 or so, leave it alone. More than that, go with a .010, or a .030 over bore.
Stock crank. Again from a BDR perspective. Leave the stocker in there, throw it on the dyno when you're all done and pulley it until it makes 515 or so RWHP. That'll probably be mid-high 400's uncorrected up there in the clouds. If you plan to keep the car, and want to go beat on it, then the forged crank might be worth it. For the 1500 miles a year that car see's right now, I dunno.
You're fuel system is good to go. Big injecotrs and that pump will support some prety good power. I dunno exactly how much, but there are some big power LS1's with similar set-ups. If you buy some kind of scanning tool, you should be able to monitor your injector pulse width. Keep your injecotrs below 85% duty cycle or so and you'll be fine. I really doubt you'll max that pump out, especially in UT. I dunno, maybe though. Check around and see what kind of HP a single walbro can support.
Block fill. Prolly over kill for you. A 1/4 fill might not be a bad idea, but I really don't think you need it. I don't think you'll run into cooling problems. If you do, they can probably be corrected with a radiator and fan combo.
If you decide to stroke it, my only hands on experience was my red vette. It had a cast SCAT crank in it and everyone told me it would handle some pretty serious power. That engine was supposedly built to take a 250 shot of dope, which should of put it up around 800 RWTQ, and 625 RWHP or so. Wether it would of taken it or not I dunno. I think you'll be fine with a cast crank, but if it's only a couple hundred bucks to go to a forged crank, why not do it? Cast parts have come a LONG way since the 60's. Most people you talk to are stuck in the mindset that all cast parts are weak. New ZO6's have cast pistons hung on freaking titanium connecting rods. Don't get me wrong, newer cast parts still aren't forged, but they don't deserve the horrible reputation their ancestors gave them.
Last thing, when asking around on the net, remeber it's a lot easier to spend other people's money. People will always recommend the high dollar safer/better option. It's up to you how much of a risk you are willing to take. if it were me, I would of pullied that thing like a madman, and hit it with an eleventy billion shot of juice, just to see how much it would take. I also would of broken it in the first week. So take anything I say with a grain of salt.
