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Edit 2: It turns out that this isn't an issue. Call the two roots on the line $\mbox{Re}(x) = 0$ $r_1$ and $r_2$. Suppose that locally, $r_1(\epsilon) = \epsilon$, $r_2(\epsilon) = i - m\epsilon + a\epsilon^k + O(\epsilon^{k+1})$, $a \ne 0$, $m > 0$. Note that if we had $r_2(\epsilon) = i-m\epsilon$, then the intersection of the halfplanes corresponding to $r_1(\epsilon), r_2(\epsilon)$ and $r_1(-\epsilon), r_2(-\epsilon)$ would be contained in the halfplane $\mbox{Re}(x) \le 0$, and the intersection of their boundaries would be located at $i/(m+1)$. Now if $k$ is even, then the correction term shifts the intersection of the boundaries by $a\epsilon^k/(m+1) + O(\epsilon^{k+1})$, so if we choose $\epsilon$ small such that $a\epsilon^k$ is real and negative, then we see that the halfplane $\mbox{Re}(x) \le 0$ is not essential. If $k$ is odd, then if we choose $\epsilon$ small such that $\mbox{Re}(\epsilon) < 0$ and $a\epsilon^k$ is a positive real times $i$, then $r_2(\epsilon)$ is shifted up and $r_2(-\epsilon)$ is shifted down, so the intersection of the boundaries will be shifted to the left (draw a picture), so again the halfplane $\mbox{Re}(x) \le 0$ is not essential.

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First, a counterexample to your conjecture. Let $\Pi = x^4+x^3+4x^2+4x = x(x+1)(x^2+4)$, so $P = 4x^3+3x^2+8x+4$. The critical values of $\omega$ are $1.06638, 3.89455 + 2.87687i, 3.89455 - 2.87687i$, and by inspection (using Mathematica) we see that for each of these values of $\omega$, $\mbox{Conv}(\Pi_\omega)$ contains a neighborhood of $0$.

Now for a calculus on convex sets. Every convex set is the intersection of a set of halfplanes. Call a halfplane in this collection essential if removing all of the halfplanes in an open set of halfplanes (in the halfplane topology) containing it from our set of halfplanes makes the intersection of the halfplanes in our set bigger. We wish to find a characterization of the essential halfplanes of $\mbox{Hull}(P)$.

First of all, I claim that any essential halfplane of $\mbox{Hull}(P)$ occurs as an essential halfplane of $\mbox{Conv}(\Pi_\omega)$ for some $\omega$. This follows from continuity - for any open set around our essential halfplane there is some $\omega$, take the limit of a subsequence of these $\omega$s...

Now, suppose that the halfplane $\mbox{Re}(x) \le 0$ occurs as an essential halfplane of some $\mbox{Conv}(\Pi_\omega)$, i.e. there are at least two roots of $\Pi_\omega$ with real part $0$, and the rest of the roots have negative real part. If the number of roots on the line $\mbox{Re}(x) = 0$ (counted with multiplicity) is two, then by holomorphicity we can always find a direction to move $\omega$ so that either both roots move to the left, or both roots stay on the line $\mbox{Re}(x) = 0$ and move towards eachother. If we can ever make both roots move to the left, then clearly the halfplane $\mbox{Re}(x) \le 0$ is not an essential halfplane of $\mbox{Hull}(P)$, otherwise we keep pushing the roots towards eachother until either they run into eachother or until a third root hits the line $\mbox{Re}(x) = 0$. In any case, we see that if a halfplane is essential for $\mbox{Hull}(P)$, then there is some $\omega$ such that the halfplane is essential for $\mbox{Conv}(\Pi_\omega)$ and such that at least three roots (counted with multiplicity) of $\Pi_\omega$ are on the boundary of the halfplane, or two of the roots are equal and $\Pi_\omega$ has no other roots.

So if we let $L$ be the set of $\omega$s such that three of the roots of $\Pi_\omega$ lie on a line, we get that $\mbox{Hull}(P) = \cap_{\omega \in L} \mbox{Conv}(\Pi_\omega)$ if $\deg P \ge 2$.

Edit: Actually, I think there is a problem with this. It's conceivable that two roots are on the line $\mbox{Re}(x) = 0$ and have derivatives (with respect to $\omega$) pointed in opposite directions, such that we can't simply push them towards eachother. For instance, the map from one root to the other root could, locally, look like the fractional linear transform sending the left halfplane to a circle contained in the right halfplane and tangent to the line $\mbox{Re}(x) = 0$ at the other root. So, we may need to enlarge the set $L$ to contain also those $\omega$s for which the ratio of the derivatives of two of the roots (with respect to $\omega$) is a negative real number.

First, a counterexample to your conjecture. Let $\Pi = x^4+x^3+4x^2+4x = x(x+1)(x^2+4)$, so $P = 4x^3+3x^2+8x+4$. The critical values of $\omega$ are $1.06638, 3.89455 + 2.87687i, 3.89455 - 2.87687i$, and by inspection (using Mathematica) we see that for each of these values of $\omega$, $\mbox{Conv}(\Pi_\omega)$ contains a neighborhood of $0$.
Now for a calculus on convex sets. Every convex set is the intersection of a set of halfplanes. Call a halfplane in this collection essential if removing all of the halfplanes in an open set of halfplanes (in the halfplane topology) containing it from our set of halfplanes makes the intersection of the halfplanes in our set bigger. We wish to find a characterization of the essential halfplanes of $\mbox{Hull}(P)$.
First of all, I claim that any essential halfplane of $\mbox{Hull}(P)$ occurs as an essential halfplane of $\mbox{Conv}(\Pi_\omega)$ for some $\omega$. This follows from continuity - for any open set around our essential halfplane there is some $\omega$, take the limit of a subsequence of these $\omega$s...
Now, suppose that the halfplane $\mbox{Re}(x) \le 0$ occurs as an essential halfplane of some $\mbox{Conv}(\Pi_\omega)$, i.e. there are at least two roots of $\Pi_\omega$ with real part $0$, and the rest of the roots have negative real part. If the number of roots on the line $\mbox{Re}(x) = 0$ (counted with multiplicity) is two, then by holomorphicity we can always find a direction to move $\omega$ so that either both roots move to the left, or both roots stay on the line $\mbox{Re}(x) = 0$ and move towards eachother. If we can ever make both roots move to the left, then clearly the halfplane $\mbox{Re}(x) \le 0$ is not an essential halfplane of $\mbox{Hull}(P)$, otherwise we keep pushing the roots towards eachother until either they run into eachother or until a third root hits the line $\mbox{Re}(x) = 0$. In any case, we see that if a halfplane is essential for $\mbox{Hull}(P)$, then there is some $\omega$ such that the halfplane is essential for $\mbox{Conv}(\Pi_\omega)$ and such that at least three roots (counted with multiplicity) of $\Pi_\omega$ are on the boundary of the halfplane, or two of the roots are equal and $\Pi_\omega$ has no other roots.
So if we let $L$ be the set of $\omega$s such that three of the roots of $\Pi_\omega$ lie on a line, we get that $\mbox{Hull}(P) = \cap_{\omega \in L} \mbox{Conv}(\Pi_\omega)$ if $\deg P \ge 2$.