This is an extended question of the classical rolling dice and give face value question.
You roll a dice, and you'll be paid by face value. If you're not satisfied, you can roll again. You are allowed $k$ rolls.
In the old question, if you are allowed two rolls, then the expected payoff is $E[\text{payoff}] = 4.25$.
If you are allowed $3$ rolls, the expected payoff is $E[\text{payoff}] = 4.67$.
If you can roll up to $50$ times, you can calculate the payoff using the formula and get $E = 5.999762$, notice that after $5^\text{th}$ roll, your expected payoff will be greater than $5$, so you'll only stop once you roll $6$.
So my question here is, without exact calculation(using geometric process), how would you estimate how many $9$s are there in the answer? Or another way to ask will be, is the expected payoff bigger than $5.9$? bigger than $5.99$? etc.
Let $a_n$ be the expected payoff of an $n$-roll game. We have $a_1=3.5$ and the recursion $$a_{n+1} = \frac{6 + \lceil a_n \rceil}{2} \cdot \frac{7 - \lceil a_n \rceil}{6} + a_n \cdot \frac{\lceil a_n \rceil - 1}{6}$$
You noted that for $n \ge 5$ we have $\lceil a_n \rceil = 6$, so the recursion in that case becomes $$a_{n+1} = 1 + a_n \cdot \frac{5}{6},\qquad n \ge 5.$$
Letting $p = 5/6$ we have we have the general formula \begin{align} a_n &= p^{n-5} a_5 + p^{n-6} + p^{n-7} + \cdots + p + 1 \\ &= p^{n-5} a_5 + \frac{1-p^{n-5}}{1-p} \\ &= (5/6)^{n-5} a_5 + 6(1-(5/6)^{n-5}) \\ &= 6 - (5/6)^{n-5} (6 - a_5) \end{align} for $n \ge 5$.
The second term $(5/6)^{n-5} (6 - a_5)$ tells you how far the expected payoff is from $6$; you can set this to $0.1$ or $0.01$ and solve for $n$ to answer your question.