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Will I hate re-gearing to 5.29?

Doubt you’ll hate it. I’m on 4.10s with 6.5 and 36” and it’s barely crawlable. It works and I certainly make due, but 5.29 would be mint. I’m a trailer queen tho. But I will say, it seems to love high r’s. I don’t have a tach, but I’ve probably floated the valves on several occasions.
It's a done deal. I think it'll be fine.

Are you in Woodbury TN? I've got people up there and we trail ride up that way every so often.
 
It should be the earlier one if it didn't get swapped at some point in its life. I've never really investigated any farther.

I had to buy a new shift tower for it a long long time ago, and I think they are different early vs late. I remember having to modify the little shifter bolt to get it to fit into my shifter, but that was probably because I ordered the wrong one or something
I know this is an old post. But to figure out if you have the early or late samurai tranny look at the drain and fill plugs on it.
Hex head plugs=early tranny=.795 5th.
Recessed square plugs=late tranny=.86 5th.
The RPM difference in 5th at 65MPH between the two is about 300RPMs.

On the shift towers, bolts and shifter slot…the later ones use a larger bolt with a bigger “nub” on the end…hence a wider shifter slot.
The shifter towers are the same other than the size of the hole for the shifter bolt.
From what I recall the shifter bolt size changed in 1990 to the larger one.
 
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I ran 37" on my 87 tin top with Toya axles and 6.5 tcase on stock 1.3 carbed. It would easily drive 70 down the highway, and creeped awesome off road. I can't remember if I had 4.88 or 5.29. The build thread was on the other forum. RIP little zukie.
 
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