Stephenseals said..foamballer said..
3. get cleaned up by a few big waves on the paddle out and get blown into the headland cliffs. Personally, I'd rather not have a pfd in this situation.
Scenario 3 looks pretty bad
I had one near miss like that... cross wind paddle to get out around a headland before the downwind run. I was at least 500m out behind the surf and still heading out but a wave just seem to break out in mid ocean and really chewed me over. When I finally got back on the board I was a lot closer to the rocks than I wanted to be given the wind strength and direction. All ended well with a bit of adrenaline fueled paddling, but something to be wary of.
Starting with the wind behind you instead of side-on is so much easier and safer.
Always plan your exit too - considering the size of the surf and tides you may encounter.