Buying used is tough in my opinion. If you don't know the seller personally, it's a crapshoot.....
Having had a few money-pits already, I think I know how you feel. I too am in the market for something...and thinking of going new. I have a 13' dory pull-start, and it's a great little boat....but my back isn't what it used to be //Sick of pulling the cord and want something bigger. There's no doubt you can negotiate the cost. It's a luxury item.
If you can afford it, which it sounds like
she said you can
...the only thing you may want to think about is not limiting yourself to 14'. If she gave you the green-light, go a little bigger. Once you're out of the bay-areas, the ocean tends to bully the smaller boats. Just my 02 cents