This problem has nothing to do with how many times you need to compile. Removing remember picture does not help. Even if you force TikZ to remake pictures by /tikz/external/remake next and compile a thousand times it will still show nothing.
The true problem is that when an externalized picture is included back to the original document, \includegraphics \pgfimage pdfTeX will clip it by its bounding box.
Since pictures with overlay has a bounding box of size zero, everything will be clipped. (See the next section)
To prove this, consider the following example:
\documentclass{book}
\usepackage{tikz}
\usetikzlibrary{external}
\tikzexternalize
\begin{document}
\tikz{
\draw circle(5);
\pgfresetboundingbox
\path(-4,-4)(4,4);
}
%\includegraphics{\jobname-figure0.pdf}
\end{document}
It will gives you the clipped circle, which is exactly the same as if you open \jobname-figure0.pdf in any pdf reader.

A more interesting example
Removing \path(-4,-4)(4,4);, you will get

This seems to contradict my theory: without (-4,-4) and (4,4) the bounding box should be of size zero. But guess what: if you open \jobname-figure0.pdf you will see exactly the same arc.
diving into PDF
- While
\jobname-figure0.pdf is generated, it has a /MediaBox entry, which is rouphly the size of the page.
- If, in TikZ,
\pgfresetboundingbox or [overlay] is used, a default value of [0 0 144 144] is used. Here 144 means 2 inches. This number comes from nowhere.
- If the bounding is set explicitly as, say,
\path(-1in,-1in)(2in,2in); then it is [0 0 216 216]. Here 216 means 3 inches.
While pdfTeX includes the external image in the main file, it
takes the BoundingBox of a pdf file from its /CropBox if available, otherwise from its /MediaBox.
- For
\pgfresetboundingbox and [overlay]: the /BBox entry is [0 0 144 144] .
- For
\path(-1in,-1in)(2in,2in);: the /BBox entry is [0 0 216 216] .
When PDF renderer renders the file, it
clips according to the form dictionary’s /BBox
- For
\pgfresetboundingbox and [overlay], everything outside (0,0) rectangle (2in,-2in) will be clipped . There is a negetive because the y-axis points down in PDF.
- To prove this, try to replace
\node at (1,1) {test2}; by ±1.
- For
\path(-1in,-1in)(2in,2in);: it is clipped with respect to the that rectangle.
Possible workaround?
There might be a way to tell pdfTeX not to set the /Bbox entry. This is quite hopeless.
The other possibility is to rewrite TikZ externalizing library so that it will produce an external image with its native bounding box. But keep the information of user-specified bounding box and use it as the image is included back.
(This could be really hard. For exmple if \tikzmark is used, what the native bounding box should be? )
For now, a easy workaround is not to export the image
\documentclass{article}
\usepackage{tikz}
\usetikzlibrary{external}\tikzexternalize
\begin{document}
\tikzset{external/export next=false}
\tikz[remember picture,overlay]\draw(0,0)--(current page.center);
\end{document}