(updated; apologies for way too much room left for interpretation in the original post)
More precisely, $\sigma(c)$ records the order of (Euclidean) distances $d(x,e_k)$ at which the standard basis vectors $e_k$ are from every $x\in c$. E.g. for $\sigma(c)=()=12 \dots n$, the identity permutation, one has $d(x,e_1)$<$d(x,e_2)$<...<$d(x,e_n)$, and the arrangement hyperplanes on the boundary of this $c$ are $H_{k,k+1}$ for $k=1,\dots ,n -1$.Let $\ell$ be a general position line in $H$. Then $\ell$ intersects $\binom{n}{2}+1$ cells. Two of these intersections are unbounded; let us denote the corresponding cells $c_0$ and $c_t$, respectively. As we follow $\ell$ from $c_0$ to $c_t$, from one cell to the next, the corresponding permutation $\sigma(c)$ \sigma(c) = i_1 i_2...$ $i_n$ changes from $\sigma(c_0)$ to $\sigma(c_t)$; namely, it gets multiplied by $(i_k,j_k)$ (i_k,i_{k+1})$ whenever we cross $H_{i_k,j_k}$. H_{i_k,i_{k+1}}$. One can also view this as flipping the adjacent entries, i.e. applying the transposition $(k,k+1)$ to the sequence $\sigma(c)$.
Assume that $\sigma(c_0)$ is the identity permutation. Then $\ell$ gives us an expression for specifies a sequence of flips $\sigma(c_t)$:(k,k+1)$ that need to be applied to obtain $$\sigma(c_t)=(i_0,j_0)\cdot \sigma(c_t)=n, n-1, n-2, \ldots 1$. E.g. for $n=3$ there are two such sequences:
Question. Are all the expressions sequences of $\sigma(c_t)$ into $\binom{n}{2}$ transpositions flips leading from $1,2, \dots, n$ to$n, n-1, n-2, \ldots 1$ realized by general position lines in $H$? EDIT: Possibly with several labelings of $H_{ij}$, not just one fixed. Note that $\sigma(c_t)$ is not arbitrary, as $\ell$ has to intersect each $H_{ij}$ on its way from $c_0$ to $c_t$.
I guess that the answer is yes they do, but to show this, one might need to apply some machinery of root systems I am not familiar with.

