Can you explain a bit more about what you mean by “way more nuanced conditions about what exact font to load”? I’ve tried both approaches recently and found using Google to be quicker and less work, but didn’t find it more nuanced or specific. What have I missed?
Google Webfonts looks at the useragent (and maybe more?) of the requester and serves different stylesheets depending on that, changing if to load WOFF or TTF fonts for example.
If you need to support browser that doesn't support woff2, Google Font do that for you automatically.
Furthermore, Google Font subsets their fonts so that if you only use English, the other parts of the font that contain Greek, etc. won't load (via unicode-range CSS)