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you would absolutely blow up the tranny that is in the truck now. if you got a mid 90's CTD you shouldn't have to do PCM work as they were still a mechanical diesel.
Those swaps took a very very long time, if you can't do the work yourself it'll cost you an insane amount. If you bother with a cummins, I'd say pull a tranny, t-case, and rear diff as well
That said, I like seeing other people try