I wonder if the problem you are having (other than simply lack of practice) is trying to get into the kayak from a dock. This is a much harder way to enter a kayak. I have a feeling that, as long as you don't mind getting your feet/shins wet, you'll have much better luck entering the kayak from the shore. Just walk in the water a little bit, turn your backside to the boat and sit down in the seat sideways, then pull your legs into the boat in front of you. If you do it this way, instead of from a dock, you are much less likely to have problems because your center of gravity is much lower, your not stepping DOWN into the boat. I have seen many kayakers flip their boats (of course, their kayaks are not usually as wide as the Outback but...) while trying to get in from the dock because they don't want to get their feet wet. Well this is a bad option because they end up getting their whole body wet instead! I say, play it safe, get your feet wet by entering from shallow water instead of the dock.
My 2 cents.
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