Here is the answer to my question in my own words.
Lemma 1: Let $G \times X \rightarrow X$ be a group action which can be realized as the action of a closed subgroup of $\textrm{GL}(V)$ on a closed orbit in projective space $\mathbb{P}(V)$, $\lambda$ a cocharacter of $T$, and $P \in X$. The morphism $k^{\ast} \rightarrow X$, $x \mapsto \lambda(x)P$ extends (uniquely) to a morphism $\mathbb{P}^1 \rightarrow X$. The points $\lambda(0)P$ and $\lambda(\infty)P$ are fixed points of $\textrm{Image } \lambda$.
Theorem: Let $\lambda$ be a regular cocharacter of $T$. Let $\mathcal B$ be the projective variety of Borel subgroups of $G$.
There exists a Borel subgroup $B(\lambda) \in \mathcal B$, together with an open neighborhood $U$ of $B(\lambda)$, such that $\lambda(\infty)B' = B(\lambda)$ for all $B' \in U$.
The group $B(\lambda)$ is unique, and it contains $T$.
For a given regular cocharacter $\lambda$, there exists a finite collection of nontrivial characters $\beta_i$, which are trivial on $R(G) \cap T$, and have the property that if $\lambda'$ is a regular cocharacter, then $B(\lambda') = B(\lambda)$ if and only if $\langle \beta_i, \lambda' \rangle > 0$ for all $i$.
If $w \in W(G,T)$, then $w.B(\lambda) = B(w.\lambda)$.
If the Weyl group of $G$ has order two, then the theorem immediately tells us that the "finite collection" of nontrivial characters $\beta_i$ can be replaced by a single character $\beta$.
The Weyl chamber of a point $B \in \mathcal B^T$ is $$\textrm{wc}(B) = \{ \lambda \in Y(T)_{\textrm{reg}} : B(\lambda) = B\}$$
The last point of the theorem, combined with the fact that $W(G,T)$ acts on $\mathcal B^T$ simply transitively, tells us that the function $\lambda \mapsto B(\lambda)$ is a $W(G,T)$-equivariant map of $Y(T)_{\textrm{reg}}$ onto the finite set $\mathcal B^T$, and that the Weyl chambers are just the fibers of this function.
If $\beta_i$ are the characters of $T$ assigned to a regular cocharacter $\lambda$ as in the statement of the theorem, then the condition that $\lambda'$ be in $\textrm{wc}(B(\lambda))$ can be rephrased as the condition that $\langle \beta_i, \lambda' \rangle$ be $ > 0$ for all $i$.
Now fix an $\alpha \in \Psi$, and let $T_{\alpha} = (\textrm{Ker } \alpha)^0$. Then $T_{\alpha}$ is a singular subtorus of $T$ of codimension one. We can talk about Weyl chambers and whatnot in the group $Z_G(T_{\alpha})$, whose Weyl group has order two. Let $B_0(\lambda)$ be the Borel subgroup assigned to $\lambda$ in the group $Z_G(T_{\alpha})$.
Lemma 2: If $B$ is a Borel subgroup of $G$ containing $T$, then $B \cap Z_G(T_{\alpha})$ is a Borel subgroup of $Z_G(T_{\alpha})$ which also contains $T$, and $\textrm{wc}(B) \subseteq \textrm{wc}(B \cap Z_G(T_{\alpha}))$.
To prove this, we identify $\mathcal B_G$ with $G/B$, and $\mathcal B_{Z_G(T_{\alpha})}$ with $Z_G(T_{\alpha})/Z_G(T_{\alpha}) \cap B$, and use the uniqueness of $B_0(\lambda)$ given in the theorem.
Now to put all this together, choose a regular cocharacter $\lambda_0$ with $\langle \alpha, \lambda_0 \rangle > 0$, and let $B_{\alpha} = B(\lambda_0) \cap Z_G(T_{\alpha})$. By the second lemma, $B_{\alpha} = B_0(\lambda_0)$, and since the Weyl group has order two, there exists a single nontrivial character $\beta$, trivial on $T \cap R(Z_G(T_{\alpha}))$ (hence trivial on $T_{\alpha}$), with the property that $\langle \beta, \lambda \rangle > 0$ if and only if $B_0(\lambda) = B_{\alpha}$.
Now, the fact that $\beta$ is trivial on $T_{\alpha}$ tells us that $T_{\alpha} \subseteq \textrm{Ker } \beta$, whence $T_{\alpha} = T_{\beta}$. Some commutative algebra argument gives us that $a \alpha = b \beta$ for some integers $a, b$, with $b$ positive. I claim that $a$ is also positive: since $B_0(\lambda_0) = B_{\alpha}$, we must have $\langle \beta, \lambda_0 \rangle > 0$. Multiplying both sides by $b$, the fact that $\langle \alpha, \lambda_0 \rangle > 0$ shows that $a$ must also be positive.
So we can just replace $\beta$ by $\alpha$ here; they serve the same function. Thus $B_0(\lambda) = B_{\alpha}$ if and only if $\langle \alpha, \lambda \rangle > 0$.
Main result: $B(\lambda) \cap Z_G(T_{\alpha}) = B_{\alpha}$ if and only if $\langle \alpha, \lambda \rangle > 0$.
Now this follows immediately from the second lemma and the statement right above, because $B(\lambda) \cap Z_G(T_{\alpha}) = B_0(\lambda)$.