I would probably sell the car that would be the easiest to replace if you have that opportunity in the future.
The Judge will probably be the hardest to replace due to it's rarity and since prices continue to rise rapidly.
The trans am will also be hard to replace, and you seem to get the most enjoyment out of it.
Next would be the 67 GTO, more rare than the 65 since the 67 is an all original HO car and the 65 has been converted to a 4 speed.
My answer is strictly based on logic, since I like 65 GTO's better than the other three.
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