Using a very hand-wavy argument, I convinced myself that if, instead of $f(x)=\ln{x}$, we let $f(x)=\sqrt{x}$, we should still get something finite and small. Wasn't really sure where to start to prove it, so ran a program to see what happens for large N instead. $$ L = \lim \limits_{N \to \infty} \sum_{n=1}^N \frac{1}{2\sqrt{n}} -\sqrt{N} $$
It seems like $L$ approaches about $-0.73018$ but couldn't really tell if it wasn't just running away to negative infinity really really slowly. What tactics might we use to prove/disprove convergence here?
Edit: I've since discovered that this number is exactly $\frac{1}{2}\zeta(\frac{1}{2})$
Use the Euler-Maclaurin formula:
$$ \sum_{n=1}^Nf'(n)=\int_1^Nf'(t)\mathrm dt+\frac12f'(1)+\color{blue}{\frac12f'(N)+\int_1^N\rho(t)f''(t)\mathrm dt}, $$
where $\rho(t)=t-\lfloor t\rfloor-1/2$. Suppose $f'$ is continuously differentiable and decreases to zero. Then because $|\rho(t)|\le1/2$ and $f''$ is nonpositive, we see that $f''\le0$ and
$$ \int_1^N|\rho(t)|f''(t)\mathrm dt\le-\frac12\int_1^Nf''(t)\mathrm dt=\frac12\big(f'(1)-f'(N)\big)\le\frac12f'(1), $$
so the blue term converges as $N\to\infty$. Therefore, we conclude the following result:
Theorem: Let $f:[1,+\infty)\mapsto[0,+\infty)$ be twice differentiable such that $f'$ is decreasing to zero and $f''$ is continuous. Then
$$ \lim_{N\to\infty}\left\{\sum_{n=1}^Nf'(n)-f(N)\right\} $$
converges.