Does the car need to stay auto? Why do you think it has an 8.8 in it? Did he say he put one in it? I have Mac shorty headers, off road H pipe, and a 5.0L T5 bellhousing for $200. Also, if you go EFI you'll need a 92-93 engine harness. I think 95-early 97 Explorer heads and intake and an E or B cam would be a good way to reach your 275hp goal.
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