It sounds to me like you've never had to repair serious collision damage in a 'glass boat...
Anyways, as a current ordinary wooden boat owner, my take on all this is that a wooden boat is more easily fixed as it slowly falls apart over the years - a plank here, a fastening there - than a 'glass boat, which could seemingly last forever and then come down with a good dose of osmosis.
As far as needing skills to fix, I'd say, for example, rebuilding the keel would take about the same level of skill for both types, but for me, I prefer the smell of wood shavings in the morning over wearing a full-body moon suit at the height of summer and getting high on thinners..
But perhaps the main reason someone might fall in love with a a really old wooden boat and attempt to rebuild it is because they can - after all, it was built by hand one-plank-at-a-time as a one-off, only-one-exactly-like-this-one original and can be fixed exactly the same way it was built. A 'glass boat can be a little more difficult (particularly if awkward, unwieldy and expensive moulds are required) and, if you do a really great job at fixing it, the boat might end up looking exactly the same as someone else's Columbia 43..
Still, there comes a time in the life of ALL old boats, both wood and 'glass, where they are just too tired to keep living. True - you could take a couple of bits of original timber or make a mould of the old 'glass boat and start anew, whichever is easier - but if not, the wooden boat still comes out best, being easier to "recycle" piece-by-piece with the rest of it on the bonfire to keep you warm at night; instead of throwing glass shards off the chain-saw everywhere and filling the local toxic waste facility with the remains many times over.
It's a good question.