When I was taking a WW class at the NOC, years ago, the instructor simply said, "if you know how to roll, and you are failing to come up for some reason, then try coming up on the other side, because something is probably hindering you on that side". Sounds overly simple but is good advice.
I probably use my stronger-side 95% of the time, but not being able to recover 5% of the time would be unacceptable to me. The more what-if situations you can handle, they safer you are.
Often, in either WW or the sea, if you are in turbulence you can wait a few moments and then try to roll again on the same side (to allow the kayak to move at the same rate as the current, flush out of turbulence, etc) but this doesn't always work if you are in big surf, are close to an obstruction (rock, etc), are dealing with very strong wind, strong current, have gear on deck that isn't allowing your kayak to capsize fully, and other reasons.
In addition to both sides, I use different rolls for different situations, but probably everything that I have so far encountered in the wild could have been handled with a standard (layback sweep) roll, storm roll, and maybe the reverse roll (for strange situations when you are pinned to the back deck in skinny water). However, that said, I'd rather paddle with someone who has a very solid roll on one or both sides than someone who knows a bunch or rolls that aren't reliable in "combat".
Rescue / Throw Bags
Paddler's Truck Rack
Bent Shaft Canoe Paddles
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