I would say that 260# is getting into clydesdale territory, but is well within the loads a wheel can handle. When I got back into cycling a couple years ago, I was 245# and hopped on my bike with old wheels that had over 50k-miles on them that had been built over 15-years ago. I was riding off kerbs, bunny-hopping potholes and running over speed-bumps at full-speed without any problems. It's more about the build-quality than specs of the wheels.
If you've had spokes come loose, that's a sign that the entire wheel was undertension; as most stock factory wheels are. This usually can be fixed by having a competent wheel-builder re-tension the wheel to the high-end of the recommended range specified by the rim-manufacturer for that model rim. Most stock wheels I've seen have only 50-60% of the necessary tension to stay true and strong.
Personally I would go with both design ideas; a deep-V rim with a high spoke-count 32-36h for the ultimate in durability. But yea, ride your stock wheels into the ground first while you have the 2nd set built by a pro.