Suppose a positive function $f:[1,\infty) \to (0,\infty)$ has $\int_1^\infty \frac{f(x)}{x} dx < +\infty$. Is it also possible that $\int_1^\infty \frac{1}{xf(x)} dx$ converges?
I can make progress when $f(x)$ is monotone decreasing. Since $f(x)/x$ is also decreasing and the improper integral converges it must hold that $\lim_{x \to \infty} xf(x)/x = \lim_{x \to \infty} f(x) = 0$. Then there exists $C > 0$ such that $f(x) < 1$ and $1/(xf(x)) > 1/x$ for $x > C$. By the comparison test the integral of $1/(xf(x))$ diverges since $\int_C^\infty dx/x = + \infty$.
Note that as $c \to \infty$,
$$\int_1^c \frac{f(x)}{x} \, dx + \int_1^c \frac{dx}{x f(x)} = \int_1^c\left(f(x) + \frac{1}{f(x)} \right) \frac{dx}{x} \geqslant 2 \int_1^c\frac{dx}{x} \to +\infty$$
Both integrals on the LHS cannot converge.