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Four speed...... A regular four speed manual? A four speed overdrive? If it's overdrive, youre not gonna get a bunch of power up hill in fourth. You're gonna substitute that with better gas mileage.
That's the problem then. It's either power or gas mileage, I'll take the later.
Fourth gear in an overdrive is geared at like .70 or .80 (not sure about the automatic), if you want the drivability of a regular automatic, just put it in 3rd...it's a 1.00.
I got a good look at the truck and just as I expected the tailpipe has been bent right where it rounds the last turn to exit the truck's right side...it's like somebody backed into something with the pipe...its only about an inch open there now. I'll probably be getting a Gibson single exit exhaust so that should solve the problem.
One way to see if this is causing your lack of power problem would be to cut the pipe off just ahead of the bend. If the truck runs stronger than before, it was not breathing correctly. If it makes no difference then the problem is elsewhere.
The tailpipe being pinched will have some effect on performance... depending on how bad it is. My 96 had the exact same kink in the exhaust when I bought it. I cut the 2nd cat off and ran 2.5" pipe through a Dynomax Super Turbo muffler and had a new tailpipe made up at the local exhaust shop. It gave me a little more mileage and power. I don't lose speed on hills unloaded, there is plenty of power. Of course mine is a manual 5 speed overdrive, and yours is an automatic. I have noticed most 300 powered trucks with auto trannys tend to be on the doggy side.