@jerdsneker I have different suggestions for the "to buy" or "not to buy." First, you can buy a boat and not know anything about sailing and learn how to sail. I did this with no regrets and it has been one of the funnest hobbies ever. Learning to do the work on a boat like what is in your picture, that is where the tough part comes in. For example, rigging, wiring, painting, maintenance... etc. Good news is, you have resources! Man you would NOT believe the help available from all the experienced sailors right here on the net. Try the forums over at sailnet and also right here too. Then you could also pickup some books, try amazon, I found several there including a don casey sailboat maintenance book that looked really good. Last, head over to youtube watch the several sailing videos up there. Don't forget sailingtexas.com ,they also have some good how to sail videos.
Now to sum it up, if you are really eager to sail, it could be a better idea to get a boat in better condition. If you want to be patient and wait a bit, you could get this one and fix it up while you read about sailing. Then you will also learn about boat maintenance as well. So it has its ups and downs. In the end, if you think you will like sailing then chances are you will. I am also a kayaker as you and got right into sailing. I've been having my little yacht since early last year and loving her since. I never even knew how to setup a headsail last year at this time. Heck I barley knew how to raise the mainsail. Now, I can tell you what every rigging line is, name a sailboat's hardware, how to tack, how to trim, the different points of sail, plus I am currently teaching a friend how to sail on his new to him Macgregor 21

He bought his boat for only $950 ready to sail with trailer, new paint and oh, a whopping 5 sails! Good deals are definitely out there. Good luck with your decision