Attempt: I don't feel comfortable that this is correct, but here we go. Because (according to Cramer), $\Xi_n$ is $Beta(1,n)$, and thus has the density $(1 - \frac{\xi}{n})^n$ with support $[0,n]$, we can conclude that every $\Xi_n$ is stochastically bounded (I think) by an exponential random variable with parameter $1$.
This is because of the inequality $-x \ge \log(1-x)$, since this implies that:
$$ -\frac{x}{n} \ge \log ( 1 - \frac{x}{n}) \iff -x \ge n \log (1 - \frac{x}{n}) \iff e^{-x} \ge \left( 1 - \frac{x}{n} \right)^n $$
where $e^{-x}$ is the PDF of an exponential(1).
The stochastic ordering doesn't seem to depend on the probabilistic dependence of the sequence of exponential random variables, so we can assume we have some sequence of $Y_n$ i.i.d. exponential(1) R.V.'s.
This is where it seems iffy to me: basically I will claim that the stochastic ordering of $\Xi_n \preceq Y_n$ for each individual $n$ somehow implies that the stochastic ordering transfers to the entire sequences of $\Xi_n$'s and $Y_n$'s.
So I believe it's the case (please correct me if I'm wrong) that some sequence of RVs $X_n$ is $O_p(1)$ if and only if for all $M>0$, $$\mathbb{P}(X_n > M \text{ i.o.}) = 0$$
So the claim is that because $\Xi_n \preceq Y_n$ for all $n$ (don't really understand how the PDF of one can uniformly dominate the PDF of another but both integrate to $1$, but whatever) that the following would hold:
$$ \mathbb{P}(\Xi_n > M \text{ i.o.}) \le \mathbb{P}(Y_n > M \text{ i.o.}) \,. $$
So we just have to show that $\mathbb{P}(Y_n > M \text{ i.o.}) = 0$ for all $M$, but that's easy (I think), since by our assumptions
$$ \mathbb{P}(Y_n > M \text{ i.o.}) =C_{\{ n_k \}}\lim_{K \to \infty} \prod_{k=1}^K \mathbb{P}(Y_{n_k} > M) =C_{\{ n_k \}}\lim_{K \to \infty} (e^{-M})^k =0$$
where $\{ n_k\}$ is some subsequence, and $C_{\{n_k\}}$ is some finite constant depending on the particular subsequence.
If anyone can fix this, or show why it's false and doomed to fail even with modifications, I would really appreciate it.
First let's go through a chain of trivialities in order to rephrase the problem in a way which makes it easier to solve (note that by definition $\Xi_n \ge 0$):
$$\Xi_n = o(\log n) \quad \iff \quad \lim_{n \to \infty} \frac{\Xi_n}{\log n} = 0 \quad \iff \quad \\ \forall \varepsilon > 0, \frac{\Xi_n}{\log n} > \varepsilon \text{ only finitely many times} \quad \iff \\ \forall \varepsilon >0, \quad \Xi_n > \varepsilon \log n \text{ only finitely many times} \,.$$
One also has that:
$$\Xi_n > \varepsilon \log n \quad \iff \quad n(1 - F(Z_n)) > \varepsilon \log n \quad \iff \quad 1 - F(Z_n) > \frac{\varepsilon \log n}{n} \\ \iff \quad F(Z_n) < 1 - \frac{\varepsilon \log n}{n} \quad \iff \quad Z_n \le \inf \left\{ y: F(y) \ge 1 - \frac{\varepsilon \log n}{n} \right\} \,. $$
Correspondingly, define for all $n$:
$$ u_n^{(\varepsilon)} = \inf \left\{ y: F(y) \ge 1 - \frac{\varepsilon \log n}{n} \right\} \,. $$
Therefore the above steps show us that:
$$\Xi_n = o(\log n) \text{ a.s.} \quad \iff \quad \mathbb{P}(\Xi_n = o(\log n)) = 1 \quad \iff \quad \\
\mathbb{P}(\forall \varepsilon > 0 , \Xi_n > \varepsilon \log n \text{ only finitely many times}) = 1 \\
\iff \mathbb{P}(\forall \varepsilon > 0, Z_n \le u_n^{(\varepsilon)} \text{ only finitely many times}) = 1 \\
\iff \mathbb{P}(\forall \varepsilon >0, Z_n \le u_n^{(\varepsilon)} \text{ infinitely often}) =0 \,. $$
Notice that we can write:
$$ \{ \forall \varepsilon >0, Z_n \le u_n^{(\varepsilon)} \text{ infinitely often} \} = \bigcap_{\varepsilon > 0} \{ Z_n \le u_n^{(\varepsilon)} \text{ infinitely often} \} \,.$$
The sequences $u_n^{(\varepsilon)}$ become uniformly larger as $\varepsilon$ decreases, so we can conclude that the events $$\{ Z_n \le u_n^{(\varepsilon)} \text{ infinitely often} \} $$ are decreasing (or at least somehow monotonic) as $\varepsilon$ goes to $0$. Therefore the probability axiom regarding monotonic sequences of events allows us to conclude that:
$$\mathbb{P}(\forall \varepsilon >0, Z_n \le u_n^{(\varepsilon)} \text{ infinitely often}) = \\
\mathbb{P} \left( \bigcap_{\varepsilon > 0} \{ Z_n \le u_n^{(\varepsilon)} \text{ infinitely often} \} \right) = \\
\mathbb{P} \left( \lim_{\varepsilon \downarrow 0} \{ Z_n \le u_n^{(\varepsilon)} \text{ infinitely often} \} \right) = \\
\lim_{\varepsilon \downarrow 0} \mathbb{P}(Z_n \le u_n^{(\varepsilon)} \text{ infinitely often}) \,.$$
Therefore it suffices to show that for all $\varepsilon >0$,
$$\mathbb{P}(Z_n \le u_n^{(\varepsilon)} \text{ infinitely often}) = 0 $$
because of course the limit of any constant sequence is the constant.
Here is somewhat of a sledgehammer result:
Theorem 4.3.1., p. 252 of Galambos, The Asymptotic Theory of Extreme Order Statistics, 2nd edition. Let $X_1, X_2, \dots$ be i.i.d. variables with common nondegenerate and continuous distribution function $F(x)$, and let $u_n$ be a nondecreasing sequence such that $n(1 - F(u_n))$ is also nondecreasing. Then, for $u_n < \sup \{ x: F(x) <1 \}$, $$\mathbb{P}(Z_n \le u_n \text{ infinitely often}) =0 \text{ or }1 $$
according as
$$\sum_{j=1}^{+\infty}[1 - F(u_j)]\exp(-j[1-F(u_j)]) < +\infty \text{ or }=+\infty \,. $$
The proof is technical and takes around five pages, but ultimately it turns out to be a corollary of one of the Borel-Cantelli lemmas. I may get around to trying to condense the proof to only use the part required for this analysis as well as only the assumptions which hold in the Gaussian case, which may be shorter (but maybe it isn't) and type it up here, but holding your breath is not recommended. Note that in this case $\omega(F)=+\infty$, so that condition is vacuous, and $n(1-F(n))$ is $\varepsilon \log n$ thus clearly non-decreasing.
Anyway the point being that, appealing to this theorem, if we can show that:
$$\sum_{j=1}^{+\infty}[1 - F(u_j^{(\varepsilon)})]\exp(-j[1-F(u_j^{(\varepsilon)})]) = \sum_{j=1}^{+\infty}\left[ \frac{\varepsilon \log j}{j} \right]\exp(-\varepsilon \log j) = \varepsilon \sum_{j=1}^{+\infty} \frac{ \log j}{j^{1 + \varepsilon}} < + \infty \,. $$
Note that since logarithmic growth is slower than any power law growth for any positive power law exponent (logarithms and exponentials are monotonicity preserving, so $\log \log n \le \alpha \log n \iff \log n \le n^{\alpha}$ and the former inequality can always be seen to hold for all $n$ large enough due to the fact that $\log n \le n$ and a change of variables), we have that:
$$ \sum_{j=1}^{+\infty} \frac{\log j}{j^{1 + \varepsilon}} \le \sum_{j=1}^{+\infty} \frac{j^{\varepsilon/2}}{j^{1 + \varepsilon}} = \sum_{j=1}^{+\infty} \frac{1}{j^{1 + \varepsilon/2}} < +\infty \,,$$
since the p-series is known to converge for all $p>1$, and $\varepsilon >0$ of course implies $1 + \varepsilon/2 > 1$.
Thus using the above theorem we have shown that for all $\varepsilon >0$, $\mathbb{P}(Z_n \le u_n^{(\varepsilon)} \text{ i.o.}) = 0$, which to recapitulate should mean that $\Xi_n = o(\log n)$ almost surely.
We need to show still that $\log \Xi_n = o(\log \log n)$. This doesn't follow from the above, since, e.g.,
$$ \frac{1}{n} \log n = o(\log n) \,, - \log n + \log \log n \not= o(\log \log n) \,. $$
However, given a sequence $x_n$, if one can show that $x_n = o( (\log n)^{\delta})$ for arbitrary $\delta >0$, then it does follow that $\log(x_n) = o(\log \log n)$. Ideally I would like to be able to show this for $\Xi_n$ using the above lemma (assuming it's even true), but am not able to (as of yet).