OK so you are trending more toward acoustic playing and the Woolson has ergonomic issues for you. That really seems to make the decision. Yes, you could always replace the SC later more easily, but it seems a boutique guitar like the Woolson may fetch more cash upon sale. (I'm not familiar with them BTW so going on what you've said previously).
What I normally suggest for these questions is to consider losing them both to theft. With the insurance money, would you replace either, both, or go in a whole different direction? That kinda tells you which decision would be most palatable after the fact. Or listing both, which one would you regret selling if it went first?
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