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Plug the vacuum hose from the transmission directly into the vacuum pump and see if it shifts. Start in first and manually shift it up. With full vacuum, it should/will go straight to 3rd gear if you put it in drive.
I suggest you check the voltage at each alternator. The regulator set point is 14.8 volts. If both alternators are operating you will see about 28 volts.
To determine if the problem is in the alternator, click HERE.
I can't speak of the light bulbs because I have never had mine out. I don't think the type is critical. I would worry more about the plastic cracking than melting. The lights are never on that long.
Probably not, the regulator has to see enough voltage from the trio to turn on and start regulating.
Initially, the voltage in the alternator is low and the light is on because it is grounded (not direct ground, there is a resistance) through the regulator. If the idle speed is a little low...
I went thru the same problem with my Deuce. All of the wheel cylinders and metal brake lines were rusted beyond repair from water intrusion. I replaced them and switched to DOT3. DOT3 absorbs water and since the water is suspended in the fluid, you can get it out when you bleed the system.
You do need to add a lubricant. When I was running Jet A in my 7.3 Power Stroke, I put 5 gallons of WVO with 25 gallons of Jet A. Realistically, you probably only need a gallon of VO. I've bought a gallon of Wesson VO at Publix and poured that in when I didn't have any WVO on hand.
Go with the historic vehicle registration if the truck and trailer are just toys. One time fee and a permanent license plate. All of the trucks and trailer I own or have owned have been registered historic.
In Florida, the permanent semi trailer tags are for trailers that are pulled by GVW registered tractors. My M915A1 and M393A2 are both registered historic and have permanent antique tags.
That's common. My passenger side alternator is the same and probably has never been rebuilt since the truck only has 28K miles. The driver side I rebuilt a few years ago and the light goes out immediately.
Keep in mind that many of the parts across the Delco SI series of alternators interchange. This is the correct part for 27SI type 100 series IR/EF alternators. It also fits Delco 10SI and 12SI alternators. You can find it by searching 39-101-3 on ebay.
I had a 1950 F-3 and there were countersunk screws attaching the brake drums to the hubs. If there are screws, they get stuck. Heat the screw head with a torch until it glows and then it will unscrew easily.