5.38 gears 33 inch tires in my 1968.

If 33's are as big as you're ever going to go I'd keep the 3.73's and fix your original problem of breaking the bleeder screws by replacing your wheel cylinders. You should only have to remove your brake drums to get at the bolts to remove them. The last ones I bought were about $8 apiece if I remember correctly. You won't need an overdrive with your 3.73's. I run 3.73's in my 75 with either 32 or 33's and I turn about 2600rpm at 65mph, just about right for me.
Your T18 idea is a good one; beefier trans and a granny low gear. With the 6.32 first gear, your Dana 18 and 3.73's will get you around 58:1 crawl ratio, not too bad for a mild trail rig/weekender. I would look for a Ford T18 as they already have the 6.5" input shaft.

Mike

 

From mid 70 through 71, Jeeps came with an offset Dana 44 with 1 piece 30 spline shafts. Just about bulletproof foe a V6 CJ on 33's.
They are kind of tough to find, since they were used such a short time.
DON'T run an offset tcase with a centered diff in a CJ5, the driveline angles will be too severe.

 

If the shoes are in good condition and dry-not gear lube soaked- and it is properly adjusted, it can and will lock the rear wheels up on dry pavement.

 

Agreed, with a V6, 33s and 3.73s, you don't need an overdrive. At 70, you're only turning 2600 RPM... a healthy V6 will run at that speed indefinitely.

I'd fix the brakes by replacing the wheel cylinders or swapping in the 11" brakes, and focus on the four-speed next. Since you have the 11" parts, buy the puller and get 'r done. The 11" brakes can use the cable parking brakes, if the backing plates have the places for the cables, levers and such. Junk the transfer case brake and install the foot pedal and parking brakes from a '72 or later.

Your best practical axle set is a Dana 30 front with 3.73s from a '72-75 CJ, and a flanged 3.73 Dana 44 from a '70-71 CJ. The front 30 should be pretty easy, but finding the rear axle could be difficult and expensive. But you can do both of these one at a time ... Note that the flanged 44 will at best have a TracLock LSD, and that will be a downgrade from a PowrLock, if you have that now. If I already had a PowrLock in the rear axle, I'd likely go full floating conversion and a front D30. http://hermtheoverdriveguy.com/?page_id=1609 Easy.

If I had open axles, I'd think about some kind of traction aid for the rear axle (LSD? Selectable?) before I worried about my axles.