I am trying to find some reasonable upper bound on $$\sum_k [0 < k\alpha \leq n] [\{k\alpha\} < 1/k]$$ where $\alpha$ is irrational, the brackets are Iverson's notation ($1$ if true, $0$ if false), and $\{x\} = x - \lfloor x \rfloor $. If we select an $n$ at random it will satisfy $\{n\alpha\} < 1/n$ about 1 in $n$ times so the summation might grow similar to $\sum_{k=1}^{\lfloor n/\alpha\rfloor} 1/k$.
I looked at the simpler case $$ S = \sum_k [0 < k\alpha \leq n] [\{k\alpha\} < \epsilon]$$ where $ 0 < \epsilon < 1$ and found
\begin{align} S &= \sum_{j,k} [0<k\alpha \leq n][k\alpha - \epsilon < j][j = \lfloor k \alpha \rfloor] \\ & =\sum_{j,k} [0<k \alpha \leq n] [k\alpha - \epsilon <j][j\leq k\alpha < j+1] \\ & =\sum_{j,k} [0<k \alpha \leq n][j \leq k\alpha < j + \epsilon] \end{align}
If $j \leq k\alpha < j+\epsilon$ and we search for the next $j$ and $k$, say $j+l_1 \leq (k+l_2)\alpha < j+l_1 + \epsilon$, and subtract we find $l_1 - \epsilon < l_2 \alpha < l_1 + \epsilon $. In other words if $l_1$ is the smallest natural number which satisfies this for some $l_2$ then all $j$'s which satisfy $j\leq k\alpha < j+\epsilon$ for some $k$ are at least $l_1$ apart. By fitting as many $j$'s as we can
\begin{equation} S \leq 1 + \left \lfloor \frac{\lfloor n/\alpha\rfloor - 1}{l_1}\right \rfloor \end{equation}
It also seems $l_1 \rightarrow \infty$ as $\epsilon \rightarrow 0$. The difficulty I've had with the first summation is $\epsilon$ is a function of $k$ which I haven't been able to handle.