Things to watch out for?

[bmac]

I'm about your size just not as fat (260). Getting in and out or back on after you flip is not too hard. The worst part is avoiding all the crap you all have sticking up all over like rod holders, fish finder, etc.

I'm only 39 so if you are old and fat maybe it would be harder.

At our size you want to get a kayak with good capacity though. If you push the envelope you could b in for staying wet all day because the yak will ride so low in the water.
I'd recommend a wilderness ride 135, tarpon 140 or 160, natIve ultimate 14.5, ocean kayak trident 15, Malibu kayak xfactor or stealth 14, or a hobie outback or pro angler if you want the best but most expensive