Crank is shot, do I stroke it or not?

For a streeter Redline HP is kinda irrelevant. First gear will often get you 60 mph.Its often 50 mph before the big cam engine even wakes up.
A streeter needs to deliver a lot of torque, way down low. You can do it with engine. Or you can do it with leverage.

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I totally agree! Redline HP is completely useless to me. What's important is what it makes when I'm cruising along. By the way, I may have a 2.47 low gear in that trans according to what my A833 transmission rebuilder said.

In a case like this if the OP were my customer I would build him a torquey stock stroke 360, rebuild the heads with a pocket port job and keep the cam in the COMP 268H range. This will make as much torque as a run of the mill 383 Chev stroker and not break the bank. Maybe while I was in the bottom end I would grind some stroker notches for a future crank upgrade. Why does it have to be the last engine the OP ever builds? Save for the future. J.Rob

That's a good point. Putting more money into the heads on a 360 build something I thought of, but I haven't discussed.

Think of it another way. Better to have done it, then questioned why you didn't. Don't settle. If the thought is already in your head, then will you kick yourself if you didn't do it.
Ever come to Phoenix? One ride and your mind will be made up, guaranteed.

Can you explain the ride to Phoenix thing?

Yep.

Go stroker. Will make more or same HP as 360 but more streetable and cruise-able.

Flat tappet hyd cam, stamped rockers, etc... will save on parts cost. Same valvetrain he would use on a 360. Same intake. Maybe bigger carb?

Trick would be to get a piston combo with his heads that he could later grow into a better head if he chooses.

See, that's where I'm leaning towards right now. I have that same mindset too. I didn't mention it, but I also have roller rockers. We haven't determined the brand of rockers. They're probably about 7 or 8 years old (that's how long that car sat before I bought it), but they look like older style Comp Cams steel rockers.

Here's what they look like (my thread actually):

http://www.forabodiesonly.com/mopar/showthread.php?t=276688

Most of these parts are things I already had, and are being reused if they're still good.