Answer: 342

Solution:

Each summand is $10^k - 1,$ so $$\begin{aligned} N &= \sum_{k=1}^{321} \left(10^k - 1\right) \\ &= \underbrace{11\ldots1}_{321}0 - 321. \end{aligned}$$

The subtraction changes only the last four digits: $1110 - 321 = 789,$ so those four digits become $0789.$ Thus $N$ consists of $318$ ones followed by $0789,$ and the digit sum is $318 + 0 + 7 + 8 + 9 = 342.$