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Other than having an auto electric shop (or Auto zone) check it out with some diagnostic tools, not much from 2000+ miles away one can see. i.e. bench test gen, reg, and batt. If they're good, then the wiring is suspect.
If you insist on DIY.
You didn't say if you're watching the charge/discharge gauge or using VA meter to determine charging? You really need to measure amps not just volts. Need a field ammeter for that.
I agree with HH and others, the regulator (case) has to be at base voltage, so it won't work "right" on the fender cover with just the terminals jumped. I think there's a "ground" terminal/screw for that, but it's been two years, since I 6 volted. That's NOT the "Batt" terminal that powers the coils. In 6, you have to think + - backwards.
The gen will output more or less linearly based on rpm, that's why there's a "regulator". If it charges at too high a voltage, like 18, it'll make the lights bright and "burn" the battery. (So that's a clue) But the regulator only intermittently starts and stops the flow to the battery based on voltage. That V lo and hi can be controlled by the adjustment of the contacts. So a smart guess it's in the regulator and the wiring of it, since you appear to be getting output from the gen. or your battery would be dead by now.
Have to be orderly in troubleshooting.
Check the battery with nothing connected for voltage, first. Better to test with a battery strength tester. Should be ~6.2 if it's charged up. If first number is something else, either it's bad or needs charged. Correct that first, then you'll know it's not the battery. There has to be good voltage to the regulator or it won't work properly.
Then you can swop out the regulator with one known to work but that won't fix a wiring issue. You have to "polarize" the field again if you take the regulator off. I'd disconnect the "unnecessary" wiring and only work with the engine wiring to make it simpler. That's how I did it to get my motor started/functioning. Then as you put back you can "ring out" each circuit for faults.
You can easily see why they got away from 6V, gens, and regs. They work good, but not everyone can make them so.

You can easily see why they got away from 6V, gens, and regs. They work good, but not everyone can make them so.
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I don't agree, 12-volt generator/regulators work on essentially the same principles as their 6-volt cousins. The major reason for the changeover to 12-volt was the increasing electrical load imposed by more electrical equipment such as A/C, power windows and seats, etc. plus probably a significant savings in the cost of copper.

So here is the report on the charging issue...this adventure started off when the old faithful voltage regulator circuit breaker contact kept sticking closed and killing the battery so I decided to simply replace it. Ordered one from Max Merritt and installed it and it worked fine for a couple of weeks.

Then it became intermittent. I pulled the cover off and the voltage regulator contacts were not lined up and that was problem so I ordered another one.

The second one didn't work at all.

Generator field anf armature voltages were as expected...tried the other voltage regulators and they did not work... spent two days trouble shooting took the car to an old school generator shop who determined that all THREE voltage regulators were bad.

Ordered one from Kanter and it worked fine.

It appears that both Merritt and Kanter use the exact same vendor so it has nothing to do with who you buy it from...

Merritt stood by their product and will refund the money.

Anyhoo... what are the chances of getting two bad voltage regulators in a row?

I get those regulators from NAPA, Echlin brand. Never got a bad one.

I always buy the generic 6 volt Echlin regulator from NAPA, and have always had good luck with them over the last 40 years.

O_D -> Disagree all you want, no need to polarize your alternator!...
Handwriting was on the wall, even if the load didn't change the world would have got away from 6V + grd. The + grds seemed to leak off faster. I can't recall how many times, nearly every, I had to charge up the old 8N before I could cut grass. Battery life just wasn't good. 6V - good for flashlights not cars. There's a 12V gen and reg on the Cad. Weighs a ton but no complaints. Packard 6V worked OK.
I had a hypothesis that the pos grnd actually made the car less susceptible to corrosion (via anodic protection) and the switch to neg possibly accelerated it (cathodic - car becomes the anode). They came a long way with corrosion protection since the early 12V days of rocker panel and headlight bucket replacement.

Parents purchased a new 1952 Packard Mayfair. My mother got the car in a divorce in 1958. She drove back from Calif. to Pa. All maint records were in glove box. Never bought a battery - it finally gave up in '59. Seven years is a good stretch even for a 12-volt system. Manufacturers have learned to make them cheaper. The electrical load started to increase in the mid-5o's and that was the reason for the 12 volt changeover. PLUS they probably did save substantially in copper usage. Memory says high-end GM went 12 volts in '53.