Given a policy $\pi$ and the improved version upon it using policy iteration $\pi'$ we have, for $\forall s \in S$, $v_{\pi'}(s)\geq v_{\pi}(s)$.
I think the way we choose $\pi'$ makes it deterministic (unless there is a tie but let's not consider it) because we take $\pi'(s) = \arg\max_{a} \mathbb{E}[R_{t+1} + \gamma v_{\pi}(S_{t+1})|S_{t}=s, A_{t}=a]$.
Following policy $\pi'$ now (in order to evaluate it), if at time step $t$ we're in state $s$, then we'll take action $a$ given by $\pi'(a|s)$ and we'll arrive at a state $s'$ while getting a reward $r$. For simplicity let's suppose the environment isn't stochastic, the initial state is the same and that the MDP is finite. Since the policy is stochastic and the initial state is the same, we'll always take the same path and evaluate the same states.
When we start evaluating for $\pi'$, the initial values for the value function $v_{\pi'}$ are $v_{\pi}(s)$. Since we have the condition $v_{\pi'}(s)\geq v_{\pi}(s)$ (because $\pi'$ is an improvement over $\pi$), those values can only increase, and since we only evaluate particular states, then only the values for these particular states will increase.
Now if we want to take improvement step $\pi'' \geq \pi'$ then this new policy will be exactly the same as $\pi'$ since the only states that saw their values increased are the ones taken by $\pi'$.
I feel I'm misundertanding something but I can't really put my finger on it so I hope you can help me figure out what I'm missing. Thank you in advance.
EDIT: Formulated my incomprehension in a clearer manner.