I want to say:
Tell Paul to send me the letter I wrote for his father.
My attempt is:
パオロさんに それ 父に 書いてあげる 手紙、出してあげると 伝えてください
Is this grammatically correct? How could it be written otherwise?
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Almost, but not quite. First of all, it's kind of a strange sentence in English. In Japanese, it is usually possible to omit one or more pieces of information and the meaning will still be clear. In this case, however, there are four different people involved: The speaker, the listener, Paul, and Paul's father. So in order to convey the exact meaning of the English, you will need to specify each of the people.
(Note: I'm not actually sure how "Paul" is most commonly written in katakana. パオロ as you have it makes it sound Italian like "Paolo". In the Bible, the apostle Paul is written as パウロ. And I myself would probably write it as ポール or ポウル. So I'm not sure which is most common, but that's another topic.)
Second, when you say "letter I wrote for his father", do you mean "for" in the sense that his father asked you to write the letter to someone else on his behalf because he couldn't/didn't want to, or that his father is the intended recipient of your letter? For the sake of simplicity, I'm going to assume the latter; if I'm wrong, please comment and I'll change it.
Here's how I'd write the whole sentence:
私が（パオロの／その）お父さんに書いた手紙を私に出すように パオロに伝えてください。 → (The letter I wrote to his/Paul's father) (send to me) (him to) ((you) please tell Paul)
Note that you could also put the パオロに at the very beginning.
So you can actually omit the "you" who is the listener, but as you can see, you need to specify that it was I who wrote the letter to his/Paul's father, and Paul needs to be told to send it to me. I think if you leave out any of these, the meaning will not be exactly as you want:
Finally, the actual grammatical mistakes are the と and あげるs that you have. The と would be for a "quotation" of words. When you want the listener to tell the third person to do something, you must use ように.
- パオロに手紙を出すと伝えてください → Please tell Paul (the words), "Send the letter".
- パオロに手紙を出すように伝えてください → Please tell Paul to (do the action of) send(ing) the letter.
You don't need the あげる in 出してあげる because that means you're doing the favour of sending a letter for someone. It would actually be 出してくれる to mean Paul is sending it as a favour for you, but because of the ように I just described, this isn't needed. You don't need the あげる in 書いてあげる unless my assumption at the beginning was incorrect, and you were actually writing the letter as a favour to Paul's father. But even if that were the case, I think there are better ways to say that.
Yo let's be polite!
When talking about someone else's father you want to use お父さん.
Your own pops is your Chichi 父.
The letter written to Paul's father = Paul (no) Otousan (ni) kaita tegami
"Send it to me please" = [it] (wo) 「watashi (ni) okutte kudasai」
Say all that to Paul = (to) Paul-san (ni) tsutaete kudasai.
パオルさんの お父さんに 書いた手紙を 私に 送ってくださいと パオルさんに 伝えてください。
The letter written for Paul's dad, "send it to me" -- say this to paul please. Or in more natural english "[please] tell paul to send me the letter written for his father"