Hey, when the Old Shoe thing popped up it was meant to be derogatory but was it in reality a back handed , albeit unintentional , compliment ?
I like old shoes.
Old shoes are comfortable.
Old shoes have character.
Keep 'em well polished and in good condition and an old shoe beats a new shoe hands down.
As for boats, for me they are meant to be holistic. Its not just how fast, its not just how roomy, its not just how big, its not just how much money. Its a combination that makes you feel good about yourself and your boat.
So does your boat make you smile ? Answer yes, then within the definition originally suggested, its not an old shoe.
“Give a man a fire and he's warm for a day, but set fire to him and he's warm for the rest of his life.” Terry Pratchett