-- Last Updated: Jun-12-13 6:25 PM EST --
A loaded kayak can help or impede a roll - really depends on the distribution of the weight. If the heaviest stuff is right on the bottom along the keel, the boat will feel like it's rolling itself if you're a proficient roller.
If the heaviest stuff is up against the deck....the boat may even feel tippy when it's upright, and will be harder to roll. Pack your boat carefully.
As to your back, there are many different rolls you can learn, and the only way to find out for your situation is to try a few, and see which one works the best. My guess would be a C-to-C roll might be a place to start, and then go from there to find what works best for you (As much as I dislike a C-to-C, it does have its place).
Get some good instruction, and you'll be OK.
Wall Mount Boat Racks
The Kayak Wing
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