A rather detailed discussion of the subject can be found in Knopp's Theory and Application of Infinite Series (see § 41)41, pp. 298-305). He mentiones that the idea of a possible boundary between convergent and divergent series was suggested by du Bois-Reymond. There are many negative (and mostly elementary) results showing that no such boundary, in whatever sense it might be defined, can exist.
Stieltjes observed that for an arbitary monotone decreasing sequence $(\epsilon_n)$ with the limit $0$, there exist a convergent series $\sum c_n$ and a divergent series $\sum d_n$ such that $c_n=\epsilon_nd_n$. (This can be easily deduced from the Abel-Dini theorem).
Pringsheim remarked that, for a convergent and a divergent series with positive terms, the ratio $c_n/d_n$ can assume all possible values, since one may have simultaneously $$\liminf\frac{c_n}{d_n}=0\qquad\mbox {and}\qquad\limsup\frac{c_n}{d_n}=\infty.$$
I like the following geometric interpretation. Given a (convergent or divergent) series $\sum a_n$, let's mark the sequence of points $(n,a_n)\in\mathbb R^2$ and join the consecutive points by straight segments. Then there is a convergent series $\sum c_n$ and a divergent series $\sum d_n$ (both with positive and monotonically decreasing terms) such that the corresponding polygonal graphs can intersect in an indefinite number of points.
The results remain essentially unaltered even if one requires that both sequences $(c_n)$ and $(d_n)$ are fully monotone, which is a very strong monotonicity assumption. This was shown by Hahn ("Über Reihen mit monoton abnehmenden Gliedern", Monatsh. für Math., Vol. 33 (1923), pp. 121-134).
