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Sorry. Final sentence should read: The second of these cancels your Term 1 the third your Term 2 and the first would cancel your Term 5 if you had the correct relation in the Weyl algebra namely [d,x]=1[d,x]=1 rather than [x,d]=1[x,d]=1.
I apologise for being scary; it is not intentional. Terms 3 and 4 should be $-((dx)(f))(m)=(-d(xf))(m)=-d((xf)(m))+(xf)(dm)$ and this is $-f(m)-xd(f(m))+(xf)(dm)$. The second of these cancels your Term 1 the third your Term 2 and the first would cancel your Term 1 if you had the correct relation in the Weyl algebra namely $[d,x]=1$ rather than $[x,d]=1$.
There are lots of questions here. What exactly do you mean by the $\mathcal{O}_X$-dual of a left $\mathcal{D}_X$-module $\mathcal{M}$? Do you mean the left $\mathcal{D}_X$-module $\mathrm{Hom}_{\mathcal{O}_X}(\mathcal{M},\mathcal{O}_X)$? What do you mean by 'construct the category of $D$-modules in a canonical way? What is non-canonical about the usual construction? I think you must mean more by 'construct the category' than I understand.
Thanks again. In fact this has made me realise that my question wasn't quite stated correctly. I really wanted to assume $Y$ is smooth rather than $X$. I think this is what I need for my claim that $\iota^\ast \mathcal{T}_X\to \mathcal{N}_{Y/X}$ is surjective. I'll edit the question. If you want to make appropriate changes/delete comments about smoothness then I'll do the same.
I see. Thanks for that reference. I'm not sure I understand where you are using $Y$ is smooth as a stronger statement than the statement that $\iota^\ast\mathcal{T}_X\to \mathcal{N}_{Y/X}$ is itself surjective.