2. This is still a big question, and we've been having a robust argument about it on GitHub [1]. It's a problem that so far has evaded an elegant solution, but usually when that's the case, it just means we haven't been creative enough about it yet! Or did you mean versioning of the data IN the config file? Can you elaborate?
2. So basically, the majority of people don't want to type version numbers (I see where they are coming from, but respectfully disagree). I'm not sure if there exists a solution in that case. As for my comment, I was really talking about both kinds of versioning. Mainly that, if my data is version 2.3.1, I'd expect that to also lock the version of TOML, requiring a new version of my data for bumps to the underlying data structure. Again syntax is the hard part, as I'm having trouble imagining a way to actually do this. Furthermore I've seen data formats in the past that let you version "parts" of a format, I personally like this, but don't think it's a good fit for TOML.
static-files = path/to/static/files
And have it work on all platforms gives a distinct advantage over specifying paths as strings.
The one exception on Windows may be paths in a CMD.EXE command line, where / may be confused for a switch character, but I would think a config file should not be passing paths on a command line but instead passing them directly into a program - and then the forward slash will work fine.