Think about your eventual plans for a boat. Are you going to be alone most of the time, bring kids or wife along?
Are you just cruising for fun, or looking to race?
Save your money, eliminate the baby steps, and buy for that eventuality.
If you can sail a 10 footer, you can sail a 14, or a 17.
That's what makes the DS such a great boat, it's big enough, but not too big. Some people buy one to start with and then move up. And many start with one and keep it forever.
After getting banged around on a smaller boat a few times, you'd probably be looking for a bigger one anyway.