Frankly, I don't even know the difference between the two. One site had the 255 rated higher, another had the 265 rated higher. Our traveling is limited to North America; the traffic monitoring is nice but not necessary; portability between cars, of course, is essential; ease of use is a must.
So, have at it. Should I save $16 and get the 255W or "splurge" on the 265W (is the upgrade to the 265W worth $16?) Or should I go for something else entirely?
P.S. I am also thinking of a remote car starter -- getting a second car soon and there's no way we're going to park both in the garage (too many things in there). So if you have suggestions for that, I'm listening.