Answer: 109

Solution:

Each term $\lfloor \log_{10}(kn) \rfloor$ is nondecreasing in $n,$ so $f$ is nondecreasing and we just locate where it passes $300.$ For $n = 100:$ the products $kn$ run from $100$ to $10^4,$ giving $\lfloor \log_{10} \rfloor = 2$ for $k \le 9,$ $3$ for $10 \le k \le 99,$ and $4$ for $k = 100,$ so $f(100) = 9 \cdot 2 + 90 \cdot 3$ $+ 4 = 292.$

For $n = 109:$ since $9 \cdot 109 = 981 \lt 1000$ and $91 \cdot 109 = 9919 \lt 10^4,$ the terms are $2$ for $k \le 9,$ $3$ for $10 \le k \le 91,$ and $4$ for $92 \le k \le 100:$ $$\begin{aligned} f(109) &= 9 \cdot 2 + 82 \cdot 3 \\ &\quad {}+ 9 \cdot 4 = 300. \end{aligned}$$ For $n = 110:$ now $91 \cdot 110 = 10010 \ge 10^4,$ so ten terms equal $4$ and $f(110) = 18 + 81 \cdot 3$ $+ 10 \cdot 4 = 301 \gt 300.$

By monotonicity, the largest valid $n$ is $109.$