Is it possible to construct a bounded positive sequence $a_i$, ($0 < a_i < K < \infty$) such that the limit of its Cesaro mean does not exist but the limit of the Cesaro mean of its Cesaro means does exist?
That is a sequence $a_i$ s.t. : $$ \nexists \lim_{n \to \infty} \frac{\sum_{i=1}^n a_i}{n} $$ but $$ \exists \lim_{N \to \infty} \frac{\sum_{n=1}^N\frac{\sum_{i=1}^n a_i}{n}}{N} $$
Of course. Such a sequence can be constructed forcing $$(-1)^n= \frac{1}{n}\sum_{k=1}^n a_k$$ so that you have $a_1=-1$, and $a_n = n(-1)^n - (a_1 + \dots +a_{n-1})$: this gives you a way to compute $\{ a_n \}_{n=1}^{\infty}$ recursively.
Obviously, if $\{ i_n \}_{n=1}^{\infty}$ is any sequence having no limit as $n \to \infty$, you can construct another sequence $\{ x_n \}_{n=1}^{\infty}$forcing $$i_n= \frac{1}{n}\sum_{k=1}^n x_k$$ In particular, you can use your previously defined $\{ a_n \}_n$ to define another $\{ a_n' \}_n$, and then $\{ a_n'' \}_n$, and so on. This allows to construct sequences such that the Cesaro mean of the Cesaro mean of the Cesaro mean of ... etcetera does not exist.