If I had a 1989 f150 with a straight 6, and a 5 speed, how hard would it be to convert it to a 302, and a 5 speed? Does the 4.9L transmission hook up to the 302? What all would I need?

 

Not very difficult, if you have any technical skills whatsoever. You'll be making a trip to the local pick-n-pull, unless you have a donor vehicle. It'll be best to find a 302 from a 87 - 91, that had a manual transmission in it, either a 5 spd or 4 spd, you just need the motor, clutch/pressure plate/flywheel assembly, the frame/motor mounts from the donor truck, and the engine wiring harness and computer. You may want to grab the exhaust off the donor truck as well as the radiator, the inlet/outlet are changed around V8 to I6. Make sure to grab a complete engine, intake, sensors, injectors, waterpump, exhaust manifolds, accessory brackets, and even the accessories themselves if it's easier for you.
The transmission will bolt right up to the 302, you may even be able to reuse your starter. Should have no troubles, so long as you have the correct flywheel for your motor, DO NOT use the one off of the 4.9L!
The frame mounts must be changed (added). The driver's side for the V8 is riveted on...the passenger's side in my experience is not.
Other than that, it is usually a pretty simple swap, that has been made a lot.

 

Why not step up to the better 5.8?