: Using the grammatically correct way or the casual way to express the same idea in another language? In casual conversation, it is perfectly fine to end a sentence with a preposition. How

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Ideally a good translation transports the original's:

meaning
style
subtext
connotations
etc.

This is usually not possible, because different languages work differently, and a translater will have to make a choice which aspect to preserve. This choice will depend on:

genre
audience
expectations of the publisher or author

What you must do in your case, only you can know.

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In general, the usual expectation for translations is that they be "invisible," that is, that they not call attention to themselves. Given that, the idiomatic expression is the correct choice. The use of formal language in a casual setting calls attention to itself in a way that is not true for the less strict phrasing.

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It is more a matter of tone, but the redundancy of applying for a job application rather than a job will be noticed.

Maintain the tone and choose the more formal one if the original is more formal.

You have many alternatives:

How many jobs have you applied for?

How many positions have you applied for?

To how many jobs have you applied?

How many jobs did you apply for?

For how many jobs did you apply?

For how many positions have you applied?

To how many positions have you applied?

How many job applications have you filled out?

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Technically, not ending a sentence with a preposition is a rule that Latin-obsessed 17th-century nerds tried to impose on the English Language, as a part of a larger attempt to make English grammar work exactly the same as Latin grammar. This rule wasn't true for English grammar before the 17th century, and doesn't really reflect modern usage either, though it is taught, and some official texts insist on it. It is perfectly alright to end sentences with prepositions. (Sources: Oxford Dictionary blog, Merriam Webster Dictionary usage notes)

To the broader question of tone vs. correctness, when translating text, you want to preserve the language register of the original text, the tone of what is being said. If you alter the register, you are changing what the situation "feels like" - you're changing who the characters are - how they talk, how they interact with each other.

In some languages and some situations, some grammatical errors are more acceptable. Those "errors" have become part of everyday usage, whereas the "correct" form is "formal". When that is the case, the usage is what it is. If your characters were speaking English, that's how they would have said it, right? They would not have used the formal form? Then don't use the formal form.

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You're up against the difference between translation and transliteration. Transliterations simply involve word for word substitution from one language to the closest available word in another. True translations should convey the meaning of the original material in a different language, that includes nuances of tone and even the use of local idioms where possible. Translations are usually better than transliterations because they convey meaning but are sometimes impossible due to the fact that not all languages have words for all the concepts that other languages have words for.

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