NOTE: I've edited the question one last time, to be much simpler, in the hopes of getting more responses.
SETUP: Let $p_n$ denote the $n$th prime, let $p_x = p_{\lceil x \rceil}$ for all $x > 0$, let $\pi(x)$ denote the prime counting function, and let $\operatorname{li}(x) = \int_0^x \frac{dt}{\log t}$ denote the logarithmic integral function.
QUESTION: Does there exist a $t \in \mathbb{R}$ such that $ \pi(x)-\frac{x}{p_{\operatorname{li}(x)}}\operatorname{li}(x) \neq O(\sqrt{x} (\log x)^t)$?
MOTIVATION:
The function $\frac{x}{p_{\operatorname{li}(x)}}\operatorname{li}(x)$ seems to approximate $\pi(x)$ much better than $\operatorname{li}(x)$ does, at least for small $x$. Note that $$\pi(x)-\frac{x}{p_{\operatorname{li}(x)}}\operatorname{li}(x) = E(x)+H(x),$$ where $E(x) = \pi(x)-\operatorname{li}(x)$ and $H(x) = \frac{\operatorname{li}(x)}{p_{\operatorname{li}(x)}}(p_{\operatorname{li}(x)}-x)\sim \frac{1}{\log(x)}(p_{\operatorname{li}(x)}-x)$, and one has $E(x)\geq 0$ if and only if $H(x) \leq 0$ (so all "interference" in $E(x)+H(x)$ is destructive). Let $\Theta$ denote the supremum of the zeros of the Riemann zeta function. Note that both $E(x)$ and $H(x)$ are $O(x^\Theta \log x)$, and neither is $O(\sqrt{x}/\log x)$.
Note that $x \geq p_y$ if and only if $\pi(x) \geq y$, for all $x, y > 0$. (This defines a monotone Galois connection from $\mathbb{R}_{>0}$ to itself, which expresses an adjoint relationship in the corresponding poset category). Thus $x \geq p_{\operatorname{li}(y)}$ if and only if $\pi(x) \geq \operatorname{li}(y)$. The quantity $p_{\operatorname{li(x)}}\pi(x) - x \operatorname{li}(x)$ is thus natural to consider---discrete on one side, continuous on the other, and involving "both sides" of the duality, not just one. If the answer to the QUESTION above is NO, then $p_{\operatorname{li}(x)}\pi(x) - x \operatorname{li}(x)$ is smaller than $x(\pi(x)-\operatorname{li}(x))$ in order of growth, which would imply that the product $p_{\operatorname{li}(x)}\pi(x)$ of the right-left adjoint pair is better approximated by $x \operatorname{li(x)}$ than either adjoint is by $x$ and $\operatorname{li(x)}$, respectively.