Yeah wiring can be really frustrating. You have to get in the right mindset to follow it through and work it out. I looked a little bit yesterday at starter wiring. Coolerman on this board is the resource you need for your early wiring harness. I included the link to his website and a wiring diagram for your truck. I saw where he mentioned that the large white wire in pre 71 went to the starter. This large white wire is the main charging wire from the alternator, to the amp meter in the dash to the starter. From there the charge goes up the big red lead to the battery. Later models ran that wire straight to the battery with a fusible link that helped protect the wiring harness from overload. May be worth the change and upgrade. According the diagram, that white wire is spliced into under the dash, covered, to feed two fuses on the fuse block and to also run to the hazard switch which is fused seperately if you have it. The two fuses look to be Horn and Headlight I suspect. This wire is where the truck should get all of its power. If it is hot for some reason there is another power wire coming off the battery somewhere.
Had another thought, is your starter wired like the picture below, because if you have the big red lead and white wire to the same lug as motor run wire, it will make the motor spin when you hook it to the battery. This would bypass the selenoid. I can't quite tell from your picture. Is the starter motor spinning, or is the engine actually turning over continuously. I think having the battery cable wrong here will spin the starter motor, but the solenoid will not engage unless power is fed to the start terminal to make the magnet energize and activate the solenoid. This makes contact internally to run the starter motor, but it also pushes the starter gear out to engage on the flywheel. If you don't have flywheel engagement, but starter motor is freely just spinning, than that is probably what is going on. Simply swap to the other bolt and see what it does.
Cruiser Wiring 1969 wiring diagram from Coolerman
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