It really depends on how much your users are in your application. It's been best to get to around 2-4 JS files, and 1-2 CSS files for some time, mainly to optimize for the number of simultaneous connections. Short of push, there's still a per-request overhead. And I think it will be a little while before typical web apps are integrated enough to utilize server-side push.
There's also the fact that some browsers (IE on < Win10) will languish for a few years, so you may still need to support them, to what extent, who knows. And until there is proper support for native module loading in the majority of browsers, we aren't likely to see separate files widely adopted again.
Beyond all of this, as stated above, caching really hasn't worked out so well in practice, and shouldn't be your main optimization unless you are building an internal application that your users regularly utilize... Of course, those are the environments most likely to let best practices slip in terms of meeting deadlines.