Watch for new files, trigger reload even if they aren't yet required

[airhorns]

Not exactly sure and need to debug further, but I think there are some circumstances where when you create a new file and start requiring it, the new file isn't in the watched set yet, and we need a manual reload to pick it up

[mrbrownt]

I've been encountering this consistently when adding new files, unfortunately the repo is private so I can't share for reproduction steps. I should be able to put together a public repo to reproduce the issue if that would help with debug.