[mfjordvald]

As has been covered the type of matching being done is easy to tell from the prefix, though, until you get used to them you will probably be checking the documentation for just what each prefix means.

The real WTF is when choosing which location is the most specific when there is a string literal and a regex match.

Ignoring ^~ locations which will always be preferred over regex the only locations that can actually be chosen over regex is exact match "=" or default string literal (no prefix) that has an exact match. This part is what is typically the real cause of "I don't know WTF is going on here."