Third response. By improving on Saúl RM's nice argument, I will show below that if $n>\exp(\exp(7812))$, then $L_n$ is not highly abundant. Under GRH, this range can be extended to $n>\exp(15667)$. With little tweaks the constants $7812$ and $15667$ can be reduced by a factor of about $6$ (see the Remark after the Theorem).
Subsequently, Terry Tao found a better method, and as a result we know that if $n$ is a prime power, then $L_n$ is highly abundant if and only if
$$n\in\{1, 2, 3, 4, 5, 7, 8, 9, 11, 13, 16, 17, 19, 23, 25, 27, 29, 31, 32, 37, 41, 43, 47, 49, 53, 59, 61, 64, 67, 81, 83, 89, 125, 127, 128, 131, 137, 139, 169\}.$$
Theorem. Assume that the prime number $p$ is such that
$p-1\in[(400/401)n,n-1]$, and $p-1$ is divisible by the first thousand primes. Then $L_n$ is not highly abundant.
Proof. We shall prove that
$$\sigma(L_n(p-1)/p)>\sigma(L_n).$$
Note that $p\in(\sqrt{n},n]$, hence $p\parallel L_n$. Let $p-1=\prod_j p_j^{s_j}$ be the prime factorization of $p-1$, and let $r_j$ be the exponent of $p_j$ in $L_n$. Then,
$$\frac{\sigma(L_n(p-1)/p)}{\sigma(L_n)}=\frac{1}{p+1}\prod_j\frac{\sigma(p_j^{r_j+s_j})}{\sigma(p_j^{r_j})},$$
hence we need that
$$\prod_j\frac{\sigma(p_j^{r_j+s_j})}{\sigma(p_j^{r_j})}>p+1.$$
Since
$$\frac{\sigma(p_j^{r_j+s_j})}{\sigma(p_j^{r_j})}=p_j^{s_j}+\frac{p_j^{s_j}-1}{p_j^{r_j+1}-1}>p_j^{s_j}+\frac{p_j^{s_j}-1}{np_j},$$
it suffices that
$$\prod_j\left(p_j^{s_j}+\frac{p_j^{s_j}-1}{np_j}\right)\geq p+1.$$
Dividing both sides by $p-1=\prod_j p^{s_j}$, this becomes
$$\prod_j\left(1+\frac{1-p_j^{-s_j}}{np_j}\right)\geq 1+\frac{2}{p-1}.$$
For this it suffices that
$$\sum_j\frac{1-p_j^{-s_j}}{np_j}\geq\frac{2}{p-1},$$
that is,
$$\sum_j\frac{1-p_j^{-s_j}}{p_j}\geq\frac{2n}{p-1}.$$
The $p_j$'s on the left-hand side include the first thousand primes, hence the sum exceeds $401/200$ according to a numerical calculation, while the right-hand side does not exceed $401/200$. The proof is complete.
Remark. The crux of the above proof is that the sum in the last display exceeds $2$. For larger exponents $s_j$, one needs fewer primes $p_j$ for this to happen. For example, it would suffice to assume that $p-1$ is divisible by the square of the first $150$ primes, or the cube of the first $90$ primes, or the fourth power of the first $70$ primes, or the eight power of the first $60$ primes.
Corollary. If $n>\exp(\exp(7812))$, then $L_n$ is not highly abundant. If we assume the Riemann hypothesis for Dirichlet $L$-functions, then the above range can be extended to $n>\exp(15667)$.
Proof. Assume that $n>\exp(\exp(7812))$, and put $m:=n/401-1$. Let $q$ denote the product of the first thousand primes. Numerical calculation shows that
$$q<\exp(7812.3)\qquad\text{and}\qquad\varphi(q)<\exp(7809.6).$$
By the Theorem above, it suffices to show that
$$\theta(n-m;q,1)\neq\theta(n;q,1).$$
Assume that the two sides are equal. Then, by Theorem 1.2 of Bennett-Martin-O'Bryant-Rechnitzer (which appeared as Illinois J. Math. 62 (2018), 427–532), we conclude that
$$\frac{m}{\varphi(q)}<\frac{n}{80\log m}.$$
In particular, $\log m<6\varphi(q)<\exp(7811.4)$, whence $n<\exp(\exp(7812))$, which is a contradiction. If we assume GRH and relax the assumption on $n$ to $n>\exp(15667)$, we use Corollary 1.1 of Lee (which appeared as Q. J. Math. 74 (2023), 1505-1533) to obtain the following strengthening of the previous display:
$$\frac{m}{\varphi(q)}<\frac{1}{4\pi}(\log n+31008)\sqrt{n}\log n.$$
In particular,
$$\sqrt{n}<\exp(7813)(\log n+31008)\log n,$$
whence $n<\exp(15667)$, which is again a contradiction.
Second response. This is an improvement of Max Alekseyev's nice counterexample. Consider $n=71$ with
$$L := L_{71} = 2^6 \cdot 3^3 \cdot 5^2 \cdot 67 \cdot 71 \cdot L',$$
where the co-factor $L'$ is coprime to listed primes. Then set
$$M := 2^8 \cdot 3^4 \cdot 5^3 \cdot 79 \cdot L'.$$
We have
$$L = 205502400\cdot L' > 204768000\cdot L' = M,$$
while
$$\sigma(L) = 771022080\cdot \sigma(L') < 771650880\cdot \sigma(L') = \sigma(M).$$
That is, $L_{71}$ is not highly abundant.
First response. I took on Terry's challenge "beat the AI". With my own little program (which is simpler than the AI's), starting from Terry's parameters, I got down to $n=13757$:
$$\{p_1,\dotsc,p_{15}\}=\{127, 131, 137, 139, 149, 151, 157, 163, 167, 173, 179, 181, 191, 193, 197\},$$
$$\{q_1,\dotsc,q_8\}=\{13553, 13679, 13691, 13709, 13721, 13729, 13751, 13757\},$$
$$\sum_{m=1}^8 \log q_m - \sum_{j=1}^{15} \log p_j = 3.4179\dotsc \times 10^{-6},$$
$$\sum_{j=1}^{15} \log(1 +\frac{1}{p_j^2+p_j}) - \sum_{m=1}^8 \log(1+\frac{1}{q_m}) = 1.5531\dotsc \times 10^{-5}.$$
Added. The following text file contains variations of the data above. It shows that $L_n$ is not highly abundant for any $19919 \leq n < 201601$.