Plumbob has the right idea. Use a kayak style anchor trolley. Pulleys fore and aft with a rope loop between. Fasten anchor to rope loop. If you have a breeze moving you around you can control boat position by moving the loop. You'll need a way to hold loop in position. Check out kayak anchoring systems online.
Have you considered an inflatable? Check out Sea Eagle and see if there's something you like. I have two and the quality and customer service are there. Less weight, less space and no trailer.
I only ate the hind legs. If you have room to cast they're fun to catch on a fly rod. Drop any kind of buggy looking thing within a foot and they're on it. Fight like a big bluegill.
I second Sea Eagle. I have a 285 and just ordered a 420. Buy a quality inflatable and don't worry about hooks. Go online and look them over.
I have a Sea Eagle 285 9' pontoon and love it. Takes waves well but doesn't care much for wind.
Same reason I got rid of my Jackson Coosa. Great kayak in the water but getting it there was too much for me. It takes two! I now have a 42lb inflatable.
Founded in 1880. Went bankrupt in 1978 and bought out by Gladding.
Takes more power to turn big tires. It's like putting in higher ratio differential gears.
I haul 2 ten foot kayaks in my 6 1/2 foot Ranger bed. Put the tailgate down and hang on a red flag. Run a rope from the front of the bed thru the side carry handles so they don't slide out.
We have owned both and I think Vibe is hard to beat for the money. Can't say I noticed much difference in tracking. Problem with the Skipjack is the seat. Couldn't stand more than 2 or 3 hours and we ordered the deluxe seats. Yellowfin seat is much more comfortable and with your weight the extra capacity of the Yellowfin would be handy. For your use you might consider a Sea Eagle inflatable. I have the 285 fishing pontoon and like it. Seems to be well made and no transport problem.
You didn't give any details but I'd be a little leery of a $40 inflatable.
Check out VIBE kayaks. Good stable kayak for the money. Also consider an inflatable. Sea Eagle makes a good quality kayak in your price range and you don't have many transportation or storage problems.
Can't imagine two fishing from a kayak. Check out Vibe kayaks or better yet look at Sea Eagle STS10 inflatable. Trolling motor powered and no transportation problems.
why not just call your game & fish dept. Either state will have a quick and accurate answer. Most have a reciprocal agreement.