If I had a good relationship with a competent repair shop, I'd love to have an old guitar.
I had a 1930s Martin 0-18 Tenor that was superb. But when the neck was clearly bowing and I heard some rattling inside, it was time to sell (disclosing issues of course). Not just because of the potential cost, but the time it would sit in repair shop, not knowing if they'd ruin the mojo, etc.
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