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My understanding was that fertig means finished and bereit means ready. However, I observe that fertig is sometimes also used to mean ready (for example here). When I want to translate the word ready, how do I know which word to use?
The specific example I’m wondering about right now is how to say
When the paperwork is ready, I will transfer the money.
Bereit has the implication of being prepared (to do something). For example, you could have prepared yourself for a marathon (training etc.) so you can then say:
Ich bin bereit für den Marathon.
You can also prepare stuff, the corresponding verb is bereiten and they share the same etymological route. E.g:
Ich bereite das Essen.
Das Essen ist (zu)bereitet. (stative passive or adjectivised participle)
Das Essen ist bereit (und kann gegessen werden). (using the actual adjective bereit)
The word fertig on the other hand means finished. Finished can mean ready for the next step, but in general the idea is that something recently has been completed. Taking the marathon example, you are bereit if you have completed your training plan and eaten lots of carbohydrates the night before. Then you go to the actual place, put on your gear, tie your running shoes and do warm-ups. Now you are fertig with your direct preparations and ready to start running.
Ich bin (mit den Vorbereitungen) fertig. Es kann losgehen.
Similarly for the food example, using fertig means that the cooking is complete. It is now ready to be eaten.
Das Essen ist fertig.
In your paperwork example, it depends on where you want to place the emphasis. Are you looking backwards once the paperwork is ready, i.e. has it been completed? Then you should use fertig.
Wenn der Papierkram fertig ist, überweise ich das Geld.
If, on the other hand, you wish to imply that the paperwork needs to go through a few more hands before the message’s recipient can enter their data, you will need bereit.
Wenn der Papierkram bereit ist, können Sie Ihre Kontonummer eintragen, und dann überweise ich Ihnen das Geld.
From the way you phrased it, fertig sounds like the better choice.
Fertig, at least in the context you give, is used to express that something is done, finished, completed; also if that means that now something new can start, with very few idiomatic exceptions (e.g. "ready, steady, go", which would be "Achtung, fertig, los!" instead of the "Achtung, bereit, los!" that we might expect. Admittedly that is a very subtle difference). The question "Are you ready?" could translate to both "Seid ihr fertig?" as well as "Seid ihr bereit?".
So the answer to your first question is likely this: use fertig if the original meaning of the English sentence describes or asks for a completed action; use bereit if it is about something that is going to happen next (in cases where you could use "prepared (for/to)" instead of "ready" in English).
Your translation request:
Wenn die Papiere fertig sind, werde ich das Geld überweisen
One is (hopefully) "bereit" at the beginning of an event, and "fertig" at the end of it.
"Bereit" means "prepared" (to go) while "fertig" means "finished," or "done" with it.
That is to say that "bereit" means "ready" in the sense of prepared, and "fertig" means "ready" in the sense of complete.
