One of the things I thought of doing was to set up an endowment to fund a cash award for the Hugo Awards, and I don't just mean The Big One. If I did it, all categories would have the same amount associated with them. Say $1,000 or so per category (Yes, even the "fan" categories), probably by specifying $X per year (adjusted for performance of the principle fund whose interest would fund the thing) divided among the categories.
I wonder if having a cash award as well as a shiny trophy associated with winning a Hugo would make the award more prestigious or less? I can certainly see the arguments against additional Hugo categories after such a time: "It would dilute the prize pool!"