You are right! There's a mistake in my previous posting concerning the signs. Unfortunately I cannot edit my own posting anymore. So here are the correct results:
\mathrm{res}_{p^0=-\omega+\mathrm{i} 0^+}=\lim_{p^0 \rightarrow -\omega + \mathrm{i} 0^+} (p^0+\omega+\mathrm{i} 0^+) \frac{\exp(-\mathrm{i} p^0 x^0)}{(p^0)^2-\omega^2+\mathrm{i} 0^+} = -\frac{\exp(+\mathrm{i} \omega x^0)}{2 \omega}.
Accordingly the correct representation of the time-ordered vacuum propagator for the free scalar field reads
D(x)=-\mathrm{i} \int_{\mathbb{R}^3} \frac{\mathrm{d}^3 \vec{p}}{(2 \pi)^3} \frac{1}{2\omega} \left [\Theta(-x^0) \exp(+\mathrm{i} p \cdot x)+\Theta(x^0) \exp(-\mathrm{i} p \cdot x) \right]_{p^0=\omega}.<br />
I've my copy of Peskin-Schroeder here now, and comparing this with his, it's correct. Note, however that he has a somewhat different notation. What I call D he calls -\mathrm{i} D_F (for Feynman propagator, which is correct since in the vacuum the time ordered propagator is identical with the Feynman operator). The question, where to put the factor \mathrm{i} is purely conventional, of course. His D is the Wightman function (fixed ordered vacuum-correlation function of the fields).
Concerning the rest of your questions: This part of Peskin-Schroeder's calculation is at least misleading (in my opinion it's even wrong), because the integral along the real axis without the \mathrm{i} 0^+ in the denominator doesn't make sense. Peskin-Schroeder is repairing this in the same section by carefully analyzing the various possibilities to choose the integration path in complex p^0 plane to circumvent the poles on the real axis. This leads to different propagators of the Klein-Gordon propagator which, of course, is not uniquely defined by its equation of motion (I'm using my convention concerning factors \pm \mathrm{i})
-(\Box+m^2) D(x)=\delta^{(4)}(x).
The reason is simple! You can take any solution of this equation, e.g., the retarded propagator, which you would use for a source emitting waves in classical physics. This function is uniquely defined by the demand that
D_{\text{ret}}(x)=0 \quad \text{for} \quad x^0<0.
Then any other function
D(x)=D_{\text{ret}}(x)+\Delta(x),
where \Delta is a solution of the homogeneous KG equation,
-(\Box+m^2) \Delta(x)=0.
So there is not only one propagator! You have, e.g., also the advanced propagator or the time-ordered (Feynman) one or the anti-time-ordered one. It depends on the context, which one to use.
You get these different propagators also in the way Peskin-Schroeder explains it, i.e., by choosing different paths in the p^0 integral or by regularizing the integrand with (small) imaginary parts in the denominator (as is also explained by Peskin and Schroeder).
Finally, when using the theorem of residues, you have to close the integration path by large semi circles (letting the radius to \infty), but this semi circle must not contribute to the integral and particularly it must not make the integral divergent. Thus you have to choose the semi circle always such that the exponential in the Fourier integral is damped (rather than exponentially raising) at infinity. Thus you have to close the path in the upper plane if x^0<0 and in the lower plane, when x^0>0. Then it depends on the choice of paths close to the real axis, i.e., how you circumvent the poles of the integrand or on the sign when regularizing the integrand with (small) imaginary parts in the denominator. So, only after choosing the exact type of propagator you want to calculate, you can give a precise meaning to that integrals and have a unique way to calculate it with the theorem of residues.
Due to this confusion, I do not recommend Peskin-Schroeder anymore as a textbook to start QFT. I find Ryder very helpful for that purpose. Later, when a bit familiar with the subject, you should read Weinberg's marvelous books. These are the best QFT texts I'm aware of.