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Take off the fan belt
Remove wires from arm and field
Wire with alligator clip on both ends, one side to arm, other side to field.

Wire from negative battery post goes where? Touch it to the arm or field side?, to see if generator spins?

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Left is field, arm is on the right side.

This picture was taken before I replaced the fan belt.

I added a new connection to the smaller wire on the arm connection because it was frayed
(Pigged a new piece in)
What is that wire for?

I realize that the ultimate solution will be to have the whole car rewired, it’s a mess down there!

When you jump arm and field, they are connected together. So it should not matter.

That being said, attaching to arm is preferable if your arm to field jumper cable is thin.

Don't forget to disconnect your existing wires.

By the way, that "smaller wire" is ground. It's not connected to the arm wire, is it?? It should run to the base of the voltage regulator.

Edit: field should be grounded not connected to power. Had it backwards.

Not sure if this helps, or is much different, but these are the instructions from the shop that rebuilt my generator when I was having issues.

1.disconnect the field wire off the generator.
2-use a jumper wire and hook to the field term, than hook it up to a ground,this will tell you if the generator is working or not.
check the output,it should go to 8volts and higher, if it doesnt than your generator isnt doing its job,,im hoping the armature that i rebuilt is holding up.
3 if the generator is working ,than your regulator maybe giving you the issue.
4.you have a spare regulator, if thats your problem,switch them out,hook up all the wires to the reg,and polorize it,,you do this by taking a jumper wire and flashing the battery to gen connection on your regulator,,,
recheck charging system...if this doesnt help you may have to bring it back and ill have to retestand reset the reg

Changing your belt shouldn't have caused issues, I don't need to tell you that, but something's going on.....

The picture was taken before I started to replace the fan belt.

The thinner wire was connected to the arm terminal

If I add another ground from the generator to the body somewhere, will that help?

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Well hold on because if you ground your armature you will never have any output. Actually you may have damaged your generator, though likely not, since the voltage should not have gotten high enough for it to even self-excite.

Just start your car and check charging as you did before, with the connections as in the photo you sent. No jumpers. The little wire is connected to a screw on the generator case, right?

Side note, your condenser should be on the armature terminal, not the field terminal.

Do you have a copy of the wiring diagram?

With stock generator wiring, there should have been a thick 10 ga wire on the ARM terminal going to regulator and a smaller wire on the FIELD terminal also going to regulator. An extra ground wire should not be needed because a separate ground wire goes from the screw threaded directly into the generator case to one of the mounting screws at the Left front fender headlight terminal block. Another wire also connects to the terminal block mounting screw and carries the ground on to the regulator.

Some regulators have a ground screw where the wire connects, others just use one of the regulator mounting screws as the connection point. That ground is for reference to ensure the regulator and generator are seeing and working with the same voltage and no voltage drop is the result of bad connections between the block, linkage, or sheet metal pieces. It should not carry much current other than perhaps a minimal amount for the field coils. The generator mounting bolts and bracket to the block are what carries the high output current from the generator to the battery ground cable to supply the car and battery.

I have the wiring diagram.

The smaller wire, the ground I guess, was connected to the arm. This is the wire I pigged with a new end using the heat shrink terminals. This is how it was before I replaced the fan belt and I took the picture so I could re assemble the same way.

The condenser ( for radio inferences) is connected to the field terminal.

Another idea, when I moved the oil filter canister, I didn’t get the cap right the first time and it leaked oil on the generator. I cleaned as best as I could, but maybe my terminals are still oily? I had to move the oil filter out of the way to rotate the generator closer to the block.

It is possible some oil got inside the generator and on the commutator and is causing issues if it got inside one of the end openings. If you have a brush cover over the end it should prevent the majority of oil from entering and the bit that did get inside would probably not cause too many problems. It would not hurt to check though if there is a cover that is removable.

The capacitor is for radio interference and as HPH said, should be connected between ground and the ARM terminal to minimize noise and whine caused by the brushes sparking.

Ok, just leave that smaller wire disconnected for testing. It should work well enough without a dedicated ground connection as it's grounded to the block.

The terminals should be clean and dry.

And again if you grounded your armature there's no way your charging system was working. It's simply not possible. So either that was disconnected, or it's so messed up in some way that it's electrically not connected even when it physically was, or it's not actually a ground wire even though it "should" be.

Read the ohms between the disconnected small wire and the bare clean metal base of the regulator. Make sure you take your reading on clean (not dirty or corroded) bare metal on both ends. What's the reading?