For corporate typefaces, I'm under the impression that a license for supplier usage is often agreed. For everything else, most font licenses model software licensing - with the exception of emoji fonts that sometimes model image permissions.
In the communication of "what a font is", there's a choice for you. That choice will frame how the user view fonts, as they try to box it into something that they are more familiar with. Technology does not solve license management, particularly outside a locked down system (i.e. an entirely different company).
If the initial price points for licensing a font were higher, I might think differently. But, they're low. It affects the wider conversation and user assumptions. The brave idea of spending money on a high quality product becomes an education piece.
Differs according to whether you're licensing or browsing. E.g. do you mean good UX / UI for marketing or licensing? With approval processes of a mid-to-large business, the "browsing" stage is typically on a different day to the "licensing" stage.
Despite browsing from an indie shop front, I often end up licensing from myfonts and font spring over individual foundry sites because:
a) predictable, e.g. it gives license details up front; b) login is quick (many sites don't offer guest login); c) quick, clutter-free page load.
Google Fonts is great for perusing / filtering. All our designers use it for browsing over our font management system. I've never seen that happen with our other font libraries.