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With just a TransGo Shift-Reprogramming Kit and the dynamic-shift-pressures in the computer jacked up a bit, the E4OD behind my buddy's turbcharged 460 in his F-250 is holding up fine so far.
Built E4OD/4R100 hold up in fully built 7.3PSD pulling trucks.
For a little 300-6, a good shift kit and some computer tweaks should be all you need. Ford made several upgrades to the E4OD over the years. I believe 96/97 are the best years, but 95 has some of the upgrades over the previous versions.
Would the upgrades also be in need of an OBD2 system? Since I have a 95' it is still OBD1. I was thinking of upgrading to an OBD2 computer just to get MAF instead of S/D, I hear you get a little better HP and TQ curve and also it is more fuel efficient. Not sure but either way does it require the upgrade to OBD2?
No, it does not. The shift kit works independently of the transmission electronics, and any competent tuning shop (you're going to need for the power yo are wanting) can increase shift firmness further in software.