Worth the effort?

I thought the jeep 5.9 had the starters on the passenger side, so there may be a difference in the blocks.
I would do a little more homework on this.

The junkyard website has the following number noted down as “manufacturer code”
300-08159 If that means anything, the engine was pulled from a Grand Cherokee Limited and is the original engine for the car. I will get new up to date pictures of the engine lifted from the body.

500 tq from a 360 ? best to stroke it if you want something you can drive everyday and have it last
Would 383 do it or is 408 the only size that's even close?
What are the reasonable max rpms of the stock 360, a 383 and 408 stroker?