$\newcommand\ket[1]{\left|#1\right>}$
TLDR: we start with $\ket{+}_L$ because $\ket{+}$ is stabilized by $X$-gate. Start with $\ket{+}_L$ does not interfere the code space. Indeed all of the measurement results are random, but the product of selected indices gives the eigenvalue of a stabilizer, which is the syndrome (eg. if one stabilizer is $IIIZZZZ$, its eigenvalue is the product of the result of the 4th-7th measurement, which must be 1, in our case).
In this discussion, we only consider the first half of the syndrome extraction, since the second half is a mere dual of the first.
We discuss why we use $\ket{+}_L$ first. The key part here is transversal CNOT implements logical transversal CNOT in CSS code (you can verify this with stabilizer formalism where the stabilizers are invariant after CNOT and the logical operators are "as if" there is a transversal logical CNOT). Thus, if we agree that transversal CNOT($\ket{\psi},\ket{+}$)=$\ket{\psi},\ket{+}$ (you can verify this yourself), then transversal CNOT_L($\ket{\psi}_L,\ket{+}_L$)=$\ket{\psi}_L,\ket{+}_L$, which preserves the code space as we don't want the syndrome extraction to disturb the code space. Another reason is, if $\ket{+}_L$ is encoded in the same code as the data qubit, it also introduces the same stabilizers as the data qubit, which is very convenient for our following discussion.
Let's consider the simplest example. Suppose the data qubit is $\ket{\psi}=\ket{0}$ and we place an ancilla that starts with $\ket{0}$ to perform CNOT($\ket{\psi},\ket{0}$) and measure on $Z$-basis the second qubit. If there is no error, the measurement will give 1 (the +1 eigenvalue of $Z$). If there is an $X$ error, the measurement will give -1 (the -1 eigenvalue of $Z$). Observe that we have indirectly measured the eigenvalue of the first qubit.
Now let's use stabilizer formalism to repeat the example above. Initially, the stabilizer generators are $[ZI,IZ]$. If there is no error, they become $[ZI,ZZ]$ after CNOT, which is equal to $[ZI,IZ]$ (up to multiplication by the first stabilizer). Now we measure $IZ$. According to Nielsen and Chuang, we should get +1, because $IZ \in <ZI,IZ>$. If there is $X$ error, the initial stabilizer generators become $[-ZI,IZ]$ since $XZX=-Z$. After CNOT, they become $[-ZI,ZZ]$, which is equal to $[-ZI,-IZ]$ (up to multiplication by the first stabilizer). Now we measure $IZ$, and we get -1 for the same reason. Observe that the stabilizers in the ancilla are the same before and after the CNOT, up to the phase of the first stabilizer.
Recall that using $\ket{+}_L$ introduces the stabilizers the same as those used in the data. From the discussion above, we roughly have the model above applied to every pair of qubits. To see this, consider the transversal CNOT gates that connect $(1,n+1),(2,n+2), \dots$ qubits, and the two qubit model we discussed above applies to every $(1,n+1),(2,n+2), \dots$ qubit pairs. Thus, intuitively, we very roughly understand how the syndromes in the data are measured in the ancilla. But why are the products of certain measurement results the syndrome?
We now make a rigorous example with stabilizer formalism with Steane 7 qubit code. We focus on the ancilla only. Suppose the first qubit has an $X$ error, then its stabilizer generators are:
$$XXXXXXX \\ IIIXXXX \\ IXXIIXX \\ XIXIXIX\\ IIIZZZZ \\ IZZIIZZ \\ -ZIZIZIZ.$$
Notice that we have an additional stabilizer $XXXXXXX$ since it stabilizes $\ket{+}_L$. After individual and separate qubit-wise measurements of $Z_1,Z_2,Z_3,Z_4$, the stabilizer generators are:
$$s_1IIIZIII (1)\\ s_2IIZIIII (2)\\ s_3IZIIIII (3)\\ s_4 ZIIIIII (4)\\s_5IIIZZZZ (5) \\ s_6IZZIIZZ (6) \\ s_7ZIZIZIZ (7),$$ where each of $s_1,s_2,s_3,s_4=-1$ or 1 with probability 1/2 and $s_5=s_6=1$ and $s_7=-1$. We obtain these stabilizer generators because the measurement operators anticommute with the first four stabilizers, so the stabilizers are destroyed and the measurement operators remain and the outcome is -1 or 1 with probability 1/2, according to Nielsen and Chuang.
Consider the measurement outcomes of measuring $Z_5,Z_6,Z_7$. Notice that $Z_5$=$(5)\cdot(6) \cdot (2) \cdot (3) \cdot (4)$, then $s_5 \cdot s_6 \cdot s_2 \cdot s_3 \cdot s_4 \cdot Z_5 \in <stabs>$, which means the fifth measurement outcome is $s_2 \cdot s_3 \cdot s_4$ since $s_5=s_6=1$. Similarly the sixth measurement outcome is $s_7 \cdot s_5 \cdot s_1 \cdot s_3 \cdot s_4=-s_1 \cdot s_3 \cdot s_4$, and the seventh measurement outcome is $s_5 \cdot s_6 \cdot s_7 \cdot s_1 \cdot s_2 \cdot s_4=-s_1 \cdot s_2 \cdot s_4$.
The measurement of the stabilizer $IIIZZZZ$ is the product of the 4th to 7th measurement result, which is $$ s_4 \cdot s_2 \cdot s_3 \cdot s_4 \cdot -s_1 \cdot s_3 \cdot s_4 \cdot -s_1 \cdot s_2 \cdot s_4=1,$$ because $s_i^2=1$. Similarly, we can check that the measurement of the stabilizer $IZZIIZZ$ is 1 and that of $ZIZIZIZ$ is -1. Therefore, the syndrome observed is [1,1,-1], or in binary, [0,0,1], which is exactly the syndrome of the error on the first qubit according to the parity-check matrix of the Hamming[7,4] code, on which the Steane 7 qubit code bases.