John,
While logic can be a strong motivator, Emotion will win over it every time.
Practical ballistics favors the 6.5x55, but It sounds to me like your heart is with the .257....
If it were me, I'd go with a medium bore. (8mm-.375) But then I'm a medium bore slut.
My best advice it to follow your heart.
Go with the .257... In the long run, you'll be glad you did!
Grasshopper