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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.
I see you have a compressor on the Dodge and a air hose ran to the towed vehicle. Hopefully the brakes were fully functional and you were not just using the air to release the spring brakes on the wrecker.
I've noticed that none of the fonts matched on any of my trucks or trailer. It seemed like they used whatever they had or maybe even sourced locally. The font that everyone said to use, didn't match what was on the truck. When I got ready to paint, I wanted to match the existing font already on...
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