14 bolt will help witht the bigger gears to get your truck moving without generating alot more heat in the trans, swap s straight forward and you can either run a conversion u joint or swap pinion yolks, neither are a big deal, as for trans cooler then hell yes, if it doesnt have it i put one on its just safe assurance, will that help fix your issues? i dont know i will tell you that you will for sure be generating alot less heat which the trans will like, but will it fix it? well i dunno none of us can be sure if your trans issues are overheating related or something that been wrong in the rebuild.