You won't find one used because they just came out with the model this year, but the 14' Venture Islay is a very cool boat and reasonably priced. I have seen them on end-of-season sales for under $1000.
I've owned close to a dozen kayaks and used many others as rentals and loaners and have become a big booster of Venture's kayaks as excellent "bang for the buck". They are made by highly respected British manufacturer P & H (who makes the Delphin that was recommended earlier) and are well designed for performance, nicely finished, a bit lighter than similarly styled boats by other marques and quite reasonably priced. You biggest problem might be finding a midwest dealer for them.
They are forgiving of a beginner but have design aspects that allow you to increase your skills -- plust they are fast boats in flat water and secure, even fun, in rough waters.
Hardshell Kayak Sail Rigs
Full Size Sail Rig
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