I bought a non-running 1958 F600 with the 292, 5 speed and Eaton 2 speed (6.33/8.81) rear axle 2.5 years ago. The engine was not running because half of the pushrods were bent, broken and laying in the lifter valley. The Y-block engines have oil passageways from the camshaft through the block and into the head and up through the rocker stands into the rocker arm shafts. Back when non-detergent oils were in use these oil passageways would become clogged with sludge and the rocker arms would gall on the rocker shafts. I had to buy a complete set of good used shafts, rockers and pushrods to get my engine running. I still didn't have any oil going to the right side so I had to look on Fleabay and find an NOS external rocker oiling kit which consists of some tubing and hollow rocker shaft mounting studs to bypass the internal oiling system. If I were you I'd pull the rocker covers and see if you actually have any oil getting to the rocker arms. And I would not even consider using non-detergent oil. Go to Y-Blocksforever
and read all about it.
Once I got the engine running I went to work on the brakes. $850 later I had working brakes. The hydrovac power booster under the cab had to be rebuilt, the rear brake linings had to be replaced and all 4 rear wheel cylinders were pitted so I had them sleeved with stainless steel sleeves.
You can replace the generator with a modern internally regulated alternator. If you google "replace generator with alternator" I'm sure you'll find 1000's of ways to do it.
Good luck!