I'm in the camp of being confused about the comparison between Wingert and Santa Cruz - totally different guitars. One's a 1-person shop, the other is a boutique, small, multi-person shop, and the guitars are sonically very different, tho it's hard to generalize across different models. Kathy's guitars won't sound like Santa Cruz, new or old, but neither will a Santa Cruz OO sound like a Santa Cruz FS, and so on.
But as far as Kathy's guitars, first of all I'd ask her what she's doing differently and what the difference would be with a newer one.
Then for what it's worth, I've played quite a lot of her guitars. A few years back - might have been the last Healdsburg Festival that was held, or the one before that - I demo'd her guitars for her, and I played 2 or 3 new ones along side my own, which is now almost 20 years old. I'd say each guitar was different, but each had the Wingert sound, and I liked them all. I think with guitars, it comes down to what you like. As far as I know, Kathy falls into Bruce's category 2 - she's not gone high production, and generally builds one guitar at a time.
Notice that Kathy makes a few different sizes as well, so if you like her guitars, but are looking for something different, I'd talk to her about what you want, maybe a different body size, maybe different woods. She has done some interesting projects to get people what they want, even building a resonator harp-guitar recently!
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