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Why do we discourage converts? I know that Naomi did so with Rus, but Moshe doesn't seem to do so with Yisro. Why wouldn't Judaism want to encourage converts? Furthermore is it a responsibility merely of the Rabbi performing the conversion or of any Jew who meets the convert (if it is the former how do we understand why Naomi dissuaded Rus)?

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The way a local Orthodox rabbi explained it to me is this:

Being Jewish is harder than being a gentile, and (for gentiles) it's totally optional. Gentiles do not need to become Jews to merit a good life and olam haba.

However, once someone does become a Jew he has greater obligations. Doing (or not doing) certain things now is a sin where it was ok before. The sinning Jew is thus in a worse place in his relationship with God than he would have been had he not converted. Conversion is also permanent; you can't decide to "go back" and thus stop sinning.

Further, being a Jew isn't always easy in the world. We're persecuted, and throwing your lot in with us signs you up for that.

So partly out of a desire to protect and partly to not increase sin, we push back to make sure the candidate knows what he's getting into and is sincere. The Rambam (Issurei Biah Chapter 14, h/t DoubleAA) says we point out some of the easier and harder mitzvot that will now become obligatory, and we inform him of punishments and rewards. If the candidate persists, we welcome him in.

This Chabad answer to a question from a prospective convert addresses some of these topics well.

Because discouragement isn't supposed to be forever -- we stop after three times (not sure where three comes from) -- I would think that it's inappropriate for people other than the rabbis approached by the prospective ger to do this discouragement. It's their job, they'll do it, and if you also do it you're adding to the obstructions. As for why Naomi did it, two thoughts: (1) the formal process may not have been so codified then, and (2) that's an awful long journey to make just to be rejected at the end. I don't think we should take Naomi as a model for how "regular Jews" should treat would-be converts today.

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+1. Note, too, about Naomi and Ruth, that my suggested answer to a related question (in a nutshell: Ruth originally underwent conversion while still a minor) would explain why Naomi took on the responsibility of trying to dissuade her - this was right around the time when she had attained legal majority. –  Alex Jun 7 '12 at 17:19
    
The Rambam you're looking for may be the beginning of Chapter 14 in Issurei Biah. Although note that he doesn't mention 3 discouragements. –  Double AA Jun 7 '12 at 17:24
    
@DoubleAA, thanks for the source! I edited to not imply that Rambam says 3 (I don't remember him doing so either; it was bad wording on my part). –  Monica Cellio Jun 7 '12 at 17:32
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I like parts of this answer but I'm not sure I understand your comment regarding Naomi. I believe she is the source for dissuading a convert in the first place. –  user1552 Jun 7 '12 at 17:48
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Of course, today with such easy access to information sometimes the convert brings it up. It's happened to me -- somebody says he's interested in converting and jumps straight to "I know you're supposed to send me away three times", at which point I tell him "not my job" and introduce him to a rabbi. –  Monica Cellio Jun 7 '12 at 18:13
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