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Some opinion say that Hashem created the world to bestow goodness on man (and couldn't just place him in the Garden of Eden because it would be "bread of shame" - that man would get things for free).

According to those opinions, why didn't Hashem just create man in such a way that "bread of shame" isn't shameful?

As man's nature is also a creation, the concept of "Nehema Dechisufa" is also a creation. Hashem could have created man, placed him in Gan Eden, not have him work, and make his nature in such a way that "free bread" is not shameful. So why place man in this world?

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According to Derech HaShem (Ramchal), Hashem created man to bestow Chesed (as you said). Ramchal continues to say that since Hashem represents the greatest perfection and good in the universe, the ultimate chesed Hashem can do is to allow man to attach (דבק) himself to G-d.

Ramchal also mentions, that as part of the learning to attach to HaShem, man needs to attain the same G-dly qualities that Hashem has (to the fullest extent possible). Once of these qualities is "independence" (G-d has no depenendence on any other entity). Therefore man must also feel independent. If man's nature nature was compelled to serve Hashem (i.e. no yetzer hara), he would not attain the more perfected (G-dly) quality of independence, and his ability to attach to Hashem would be diminished, and consequently it would diminish G-d's ability to bestow chessed on man.

The above is my best effort to paraphrase Derech Hashem. I highly recommend you read it (it's a wonderful work), and you will find the answer to your question in the first chapter.

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    It is available here: books.google.co.il/…
    – Hacham Gabriel
    Apr 9, 2012 at 21:41
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    Why would a lack of perfection (or even more so, his ability to attach himself to Hashem) deny Hashem the ability to bestow chesed? Hashem can do anything, so why could he have not made humans (perfectly) happy without being perfectly attached to Hashem?
    – Am Haaretz Gamur Mideoraysa
    Apr 9, 2012 at 22:55
  • @AmHaaretzGamurMideoraysa: Hashem has the ability to do anything. Hashem chose to create us this way. To answer your comment, I would say that Hashem created us perfectly by creating us with imperfections that we have to rectify. Isn't that a more meaningful creation, than one which automatically does His bidding?
    – Sam Goldberg
    Apr 10, 2012 at 13:51
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    "Hashem chose to create us this way." - My question is "why"? Hashem could have created the world in a way that being a robot is the most meaningful thing anything could be, and he could be kind to humanity without humans having to fix themselves?
    – Am Haaretz Gamur Mideoraysa
    Apr 10, 2012 at 17:45
  • "He could be kind to humanity without humans having to fix themselves"... if Hashem did that, he wouldn't be bestowing his divine quality of independence on us, which would be less kind. That is Ramchal's explanation of why. Perhaps there are others. Could Hashem have created the world differently than it is? Of course. But we assume that Hashem in his perfection, created the world in the most perfect way possible. So any different form of creation (other than what was or is), is purely imaginary. Sorry that this a tautology - but whenever we talk at this level, tautology is unavoidable.
    – Sam Goldberg
    Apr 10, 2012 at 18:36

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