> But isn't 2 water bottles in a land fill orders of magnitude better than 300?

I think you're making a lot more assumptions than you think:

For example, glass vs glass: My single-use glass container may be recyclable, but the fancy glass reusable one isn't.

Aluminum: Aluminum cans are highly recyclable. Is your metal reusable water bottle recyclable?

Plastic: Ooooh, I won't go there.