This is the part that I disagree with. Those first buildings on the Songhees looked unattractive and dated right out of the box. The worst culprits over there are terrific examples of the sort of cheap and generic resort architecture that I despise so strongly. It's supposed to look prestigious, but it actually looks faux (not genuine). It's supposed to seem as if Victoria had provided some sort of unique inspiration for it, and yet you can find virtually indistinguishable stuff in Vancouver, or Whistler, or Kelowna, or Anaheim, CA, or a hundred other places.
So most of the (Songhees) buildings now look unattractive and dated. Such is the fate of most architecture.
The modern wing on the Laurel Point Inn still looks great, don't you think? It's a contemporary of the first Songhees buildings. Glassy buildings tend to age very well.
But as you say, more money buys better materials and (often, but not always) a better design.