Thanks all, the key was my wife liking the idea of a used boat and what she saw. I was surprised she is willing and interested as I've shown her a fair amount of options. I don't think the drive is a big deal, and given to poorly maintained local options this is hopefully a step in the right direction.
I have mixed feelings as I really do enjoy my 25 and it is cheap and comfortable. But my wife doesn't like it and wasn't comfortable on it last year. So this is more about getting her on a large enough boat that could be an overnight trip and comfotable in moderate winds. I expect I'll miss being able to sail in the ridiculous low wind conditions we have here often, but that is a trade off.
That C34 site is a big selling point for sure. A ton of lessons to learn and look out for.
@Stu Jackson amazing job