Regarding yout oil lines, they leak probably from rust, if you intend on keeping the jeep for a long time (I generally keep my vehicles 20+ years) replace the whole line with a conversion fitting like to a -6 or -8 and then run braided stainless lines. after this replacement, I have never had a failure and generally cost s little less than the pre-bent stainless lines. For an even cheaper method, you could go with brarb fittings and press on hose, just not as pretty or trick and I am not a fan of barb fittings on a pressure line.
As for your trans issues, to be honest, sounds like it might just be time of a re-build. My thinking in the front pump is lacking fluid after rest, similar to what was dscribed above, but with out being able to drive, hard to diagnos.