J/V... you made a lot of good points to consider, and I agree with them. I considered the 265 Express too, but for many of the reasons you mentioned, chose another Sailfish (I had a '93 Sailfish for about 12 years).
My wife is my main fishing partner, and we have fished, (and caught)
a lot of fish on the Sailfish; drifting, trolling, and chunking while anchored. I have even had tuna walk me completely around the boat, while anchored, and I successfully boated him even after getting wrapped around the anchor line. :shock:
Being in our 60's, I am concerned with my wife having safe access to the bow, on an everyday basis for line handling, as well as when anchoring. For that reason alone, I didn't want a smaller express-style boat, but also wanted the better cabin, and aft berth.
In the end, both boats are excellent fishing boats, so get on each, look'em over good, and see what works best for you.