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Just curious, what gears are in the truck? If the 300 has some work done, and it's still losing on hills, sounds to me like you're overgeared. Putting a 302 in there is going to make it that much worse due to the 302's lack of low end torque and love of rpm.
Putting in a 302 is no different than a 351, different mount stands/mounts, rad and flywheel.
Those were interesting stats on the 302 vs. the 300. My dad has an 85 with a 300 (carbed) and a manual transmission (4 speed) 2wd. The thing has a ton of pulling power but it's slower than slow. I remember when it had 31" tires on it if I was on the highway doing 60mph in OD and then the road grade increased it would struggle to maintain the current speed.
My truck is an 86 302 4x4 with an AOD. Granted it's a shortbed and my dad's is full size but I have 4x4 and he doesn't so the weights might be pretty similar. My truck feels a lot faster than his but it definitely feels less torquey. I'm pretty confident the rear in my truck is stock and I know for a fact his is. Maybe it's just me or perhaps the EFI vs. carb really makes a difference?
The EFI increased Horsepower and torque for both engines when they were introduced.
Just adding the EFI exaust manifold to the 300 increases horsepower and torque as the stock carb exaust manifold is too flow restricted. More info on the inline six forum about this swap.
As for the rear end ratios. That will definately change things at the rear wheels. Too high of gearing will throw all the torque out the window, and the performance will suffer greatly. Most of these trucks came with 2.46 or 2.75 rear end ratios stock with 4 speed ODs. Good for gas mileage (which was the aim at the time right after the 1973 and 1979 oil energy crisis) but poor on perfomance.
Mine with the 300, mated to the borg/warner T18 and 2.75 rear end is respectable, but it won't spin the tires etc... Too high of a rear end for that. But for the way I drive it's perfect for me. Now if it had 3.25's or 3.55s, or equivalent, I would need to buy tires every six months. Just remember though, you can go too low the oposite way too. My 1973 302, with t18 and 4.11 gears would light fire trails with the tires, but it's top speed was 65.
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