Value is what counts for me
At the end of the day, its value that counts.
I think that the 8 speed would use less fuel on the open road when not trailering. Because I think the motor revs are lower. But when trailering, that advantage on the open road would not be there IMO.
So, really, have your wants ticked off, and then compare the prices. And the history and warranty of the vehicle. Big price differences and low mileages should be an influence IMO. Except, if you are going to do high mileages. There is likely little point in paying a premium to get a vehicle which has 20k less mileage, if your going to do high mileages yourself. And the type of mileage can be found too ... dealers can ask the owner ... i did that with a lexus, and the owner lived on the Mornington peninsula. The dealer gave me a contact number after checking with the owner.
From the sound of this thread, 8 speeds will be easier to sell ... and they are later vehicles, with perhaps, some extras included. But - that comes down to your check box.
Incidentally the 2.7 should not be discounted for off road capability. It can run 17" wheels, which is a big advantage IMO. I know someone who has a 2.7, I think financed. His wife has "stolen" it ... but vehicles out of lease would be ideal. At 3 years, those would be 2012 ones. Typically an out of lease would be better value than one that is not?