I know there will be a lot of kayakers who will disagree with me, but my take on this subject is that if you want to go sailing, buy, or rent a sailboat. If you want to go paddling, buy, or rent a real kayak. I wouldn't buy a sailboat and then look for the best paddle for it--although it might have to be paddled, or rowed if it doesn't have an engine.
I used to say that sailing was the most fun you could have with your clothes on. Why did I say that? I don't know. I do know that I am more addicted to kayaking than I ever was to sailing. I really loved sailing, but sailing definitely depends on the cooperation of the wind gods. Paddling only depends on you and your paddle.