$\DeclareMathOperator\Tr{Tr}$Let $A_i$ with $i=1,\dotsc,N$ and $p$ be real $M\times M$ matrices. Further, let $p$ be positive definite, i.e., $p\succ 0$, with $\Tr(p)=1$. Let $0< a_i<1$ and $\sum_{i=1}^N a_i = 1$.
Claim: $$\Tr( A_1 p^{a_1} A_2 p^{a_2} \dotsm A_N p^{a_N} ) \leq \lVert A_1\rVert \lVert A_2\rVert\dotsm \lVert A_N\rVert.$$
Here, $\lVert X\rVert$ denotes the operator norm of $X$ (= largest singular value).
Can you prove this claim (at least for symmetric matrices $A_i$)? It is trivial for $N=1$: $\Tr(A p)=\sum_i A_{i,i} p_i\leq \lVert A\rVert\sum_i p_i = \lVert A\rVert$, where I used the representation of $A$ in the eigenbasis of $p$.
The claim even seems to hold if one uses N different matrices $p_i\succ 0$, $\Tr(p_i)=1$ on the left-hand side of the claim.