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This sentence comes from a question in my JLPT practise book that is part of an explanation of the use of ものなら:

一度{いちど}仕事{しごと}を手伝{てつだ}おうものなら、それをいいことにあの人{ひと}は何度{なんど}でも頼{たの}んでくるから、気{き}をつけたほうがいい。

My fractured translation is, "If helping out a little is something you intend / that's something good / asking that person's help / you should take care."

As you can see, though, I can't make the connection between asking for help and why one should take care.

What exactly is this sentence saying, and how does it relate to the use of ものなら?

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I would translate that as "If he can get your help with ease, he will ask you more and more later on, so please take care of that" or kind of. –  YOU Nov 28 '11 at 5:50
    
@YOU: So それをいいことに means "with ease"? –  Dave M G Nov 28 '11 at 5:58
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@DaveMG According to Space ALC it can mean "because of such favorable circumstances", but I don't know if that's applicable here. "because of such favorable treatment" might be better maybe? –  cypher Nov 29 '11 at 1:58
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@DaveMG it is also often used as "use it (some bad thing) as an opportunity" when being optimistic or "exploiting/taking advantage" when being kind of negative (as in this case). Often with して as "それをいいことにして". –  jlptn1 Nov 29 '11 at 4:10

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up vote 2 down vote accepted

From JGram: ~う/ようものなら: もし~ようなことをしたら...(大変なことになる) Once if (one) happen to ... , then (bad consequence)."

So the first part of the sentence does not imply the listener is the subject, but the 'that person' in the next part of the sentence instead.

So basically it is saying: "You should be careful because if you help that guy out once, he will take advantage of that (act) and ask for favors very often."

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This made me double check the meaning of ものなら and I realized my translation was wrong. I'll update it. –  jlptn1 Nov 28 '11 at 6:37
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Also its good to note my stumblings - ものなら has more than one use - Here it is with a volitional verb, which means "once you do X then Y (bad thing) will happen." But with a potential verb before it as in XできるものならY it means you don't think X is possible, but hypothetically if it were, Y. –  jlptn1 Nov 28 '11 at 7:21

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