1966 Cruise-O-Matic
On transmission fluid: I know some say that Dexron is OK, but not for me. Ford type FA is what I use and I am very sure it is the fluid required. I know GM fluid should not be used. Why mess with something that is questionable?
Convertible top: Has the top motor/pump been replaced? The new pumps have a smaller pump than original and are slower. That cannot be helped. I've had trouble with the newer motor circuit breaker. As you have experienced, they will shut down mid-cycle. I've taken the motors apart and modified the circuit breaker to delay the shut down. I want it to go thru full cycle without stopping. I think the circuit breaker is your whole problem. One thing I've thought of doing is to put the circuit breaker in the ground circuit of the motor as Ford did in earlier (61, 62) years and completely disable the enclosed circuit breaker. Do you have a top circuit breaker under the hood? If so, I'd check it..
Turn signals: When you use the word "blinker", do you mean the lights in the bumper or the fender mounted indicator lights? If you refer to the lights in the bumper, you may have a problem with the turn signal relay in the trunk. Which would be simply not feeding that light. Reference
"the lights on the right side light up when the headlights are on" - -I think you mean the light in the bumper. ? Are you seeing the turn signal light or the parking light. When the headlights are on, does the bumper light stay on or flash? I would disconnect the right side bumper light and check the circuit for power in that circuit under the hood. The wires are easily reached and can be tested at the plug. Do the fender mounted turn signal indicators work properly?
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