I can see some really good uses for something like Monero - for example, purchasing a VPS anonymously. I would definitely consider that a desirable thing to be able to do. And I know at least a few VPS providers take Monero, so we're all good right?

No. Here's the rub... the problem I see, and what makes Monero less usable to my way of thinking, is the "last mile" problem of getting value in and out of the Monero ecosystem. In my case, specifically, the question of how I transfer value I currently hold - which is almost 100% in fiat currency (USD) - into Monero, in an anonymous fashion. Yes, it can be done. No, it's not easy. And then for the merchant who accepts Monero, they probably have the inverse problem of exchanging their Monero for the desired fiat currency (which you still need to buy most things) without revealing information they may not want to reveal.