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The gears would be an easier swap. I'm sure a 360 engine would be rather hard. You would need a new trans, I think. New wires and random odds and ends. If its a DD, you probable can't put it on jack stands for a month or more. If it were me I would put in the gears and then if that wasn't enough I'd swap in a 4.0.
I think I have decided to swap in the full width D44s, add 5.38s. And in the meanwhile, I am going to rebuild the 360, get it all cherry, and then when the 2.5L hits its last trail, I will swap in the refreshened 360.
Honestly, Ive got the truck stripped all but the rear axle, the 360, th400, quadra-crap, and front d44 all setting in the garage floor, and I didnt have a clue wether to go thru with the whole swap or do it in stages....I think stages would be better. Starting with the axle/gear swap.
I think I have decided to swap in the full width D44s, add 5.38s. And in the meanwhile, I am going to rebuild the 360, get it all cherry, and then when the 2.5L hits its last trail, I will swap in the refreshened 360.
Have you thought of going Chevy 350? I looked at both before I did my swap and found that parts to do the swap to a 350 were much more available, fit better, and required minimal custom work. Plus if you want to squizze more horses out down the road there are more mods for the 350 than any other engine out there. Anyway, in case you're interested 89XJ, Chevy 350, AX15, NP231, D30 front, D44 rear.