Losing weight and getting stronger will help for sure. But as you stated what you really need is a sit on top boat. It's a night and day difference.
If I had to float a sit in all the time no doubt in my mind I wouldn't fish near as much!!!

 

yes, get the SOT and things will be easier.

 

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Get a SOT they are much easier. I have a sit in and it's awful to get out of.

 

If there is something level to the yak like a dock or log. Place the paddle behind you getting in or out of the yak and use your arms to stabilize your body while hopping in/across to the yak with the paddle.

 

Pull up to the dock and roll it over and drop out. Works every time.

 

1st off how are you to trying enter your kayak? From the shore, from a dock, from a bank, in the rocks. For the most part they are all similar but different. Normally I put my paddle across the kayak just behind your seat. With the longer portion of the paddle resting on the bank or ramp. Enter your Yak by holding the paddle behind your back. Basicly the paddle is a long board to balance yourself as you enter. You put your weight on the paddle to balance yourself. The slide down in and move the paddle to your front side. Steep bank entries are a little more complex but once you master the normal ones it comes easier. The longer and narrower your kayak the more practice it takes. Short wide kayaks are easier. After you figure out the basics.

 

Watch this video towards the end is what I'm talking about.

 

The SOT won't be until next year at best. At least the water is warm now so I can try the roll out option I guess.

 

I just picked up the perception striker 11.5, if you're looking for something that focuses on steady vs. fast take a look. Very easy to get in and out of.

 

Edgar, I usually just walk my SOT out about knee deep sit down side saddle/perpendicular and swing my legs over. Fron a dock I do something similar with my legs on the dock. I habe no experience with a SINK, but imagine it is much more difficult.

 

Im not wuite that heavy, I still always hated getting out of my sit in kayak ...my solution was that I got two square throwable boat seat cushions... just put them on the seat in the kayak and it Raises your butt up a good six or 8 inches ...it makes it a little easier but like others have said, a sit on top kayak is the ultimate solution