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I was where you are at about a year ago except I had not done a lot of fishing it just seemed like a great idea and a good alternative to buying a boat. So looked around and found that Southwestern college offerd a kayak class out on the strand on the bay side. All the questions that you are asking are great questions, if you buy the right yak you should never rollover, but what if you do. You can learn the basics, like reentering you kayak if you fall out, which side to enter it from, down wind side, what happens if you lose you paddle, and you will get a taste of paddling for a cheap price.
Once you get all that figured out you can work on keeping your gear on the boat, but as we all do at some time a sacrifice to the sea of a knife, pliers, rod, or what have you is the cost of doing business four inches off the water and being in the game.
If you decide to say the hell with it and take the plunge I would suggest the bay for your first couple runs or some fresh water fishing for bass or trout. My kid peddles around Otay all the time and usually does well.
Once you are ready for a try at La Jolla hiring a guide or hooking up with someone else that has some experience is a great idea. Ask around and you will get a couple of referrals for a guide or two.
Now if you are still reading the next big question you have to ask is which Kayak. Now after finishing that paddling class I went over to Fastlane Kayak and tried a Hobie, and the deal was done. If you can't afford a new one then shop craigslist and something will show up. Peddle vs Paddle is the question that you have to answer.
By the way I have 4 hobies, two of my sons fish with me, the youngest is all in to fishing, my third one is a little hestitant about fishing, but you never know when the bug will bite. To be honest I suck at fishing but I love the fact that I am four inches above the water and getting the crap scared out of me when a seal pops his head up two feet away, or dolphins break water right next to you. I have not caught the trophy fish yet but I will, who cares when, the boys and I will be on the water hopefully for years to come, and maybe their kids. That is if the MLPA will let us.....but that is a whole nother story.
Best of luck
Kayak Rookie
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