Here is a picture from an Oxford University Press publication, showing two images a small one at the left and a larger one at the right. The unusual part is that the caption of the right image is also placed on the left page.

I am sure there might be another way and I tried a couple, but in order to achieve the layout, I placed the captions using the header of the left page.
There are two issues that concern me.
First is to ensure that no more than one image floats on the left page (otherwise the captions will all go amiss). To try and prevent it I have set, the
\topnumber=1. I would however like to have this one changed later on. At what point will it be safe to change it?Adding the images to the List of Figures (can't use normal techniques) since both captions appear on the same page, but the images on different pages.
My aim is to have a fully automated solution without any author intervention other than to type the relevant two-image macro \doubletakeimage{matron}{stuartpearson}.
The MWE is simplified a bit, as I took out the width and height calculations as well as additional formatting commands. Also the captions are currently fixed for ease of readability and specified in the ps@caption command.
\documentclass{book}
\makeatletter
\usepackage[showframe=true]{geometry}
\newgeometry{left=74.8mm,top=27.4mm,headsep=2\baselineskip,%
marginparsep=8.2mm,marginparwidth=49.4mm,textheight=49\baselineskip,headheight=\baselineskip}
\@twosidefalse \@mparswitchfalse % one side option
\reversemarginpar
%% Stick the caption in the head might as well place the first picture also?
\def\asidecaption{\parbox{4.2cm}{{\bfseries Image \thefigure}\par\lorem}%
}
\def\ps@caption{%
\let\@oddfoot\@empty\let\@evenfoot\@empty%
\def\@evenhead{%
\begin{picture}(0,0)%
\refstepcounter{figure}
\put(-150,-80){\asidecaption\par}%
\refstepcounter{figure}
\put(-150,-370){\asidecaption}%
\end{picture}%
}%
\let\@oddhead\@evenhead%
\let\@mkboth\@gobbletwo%
\let\chaptermark\@gobble%
\let\sectionmark\@gobble%
}
\def\doubletakeimage#1#2{%
\renewcommand{\topfraction}{.95} % ensure seecond image will not float away
\begin{figure}[t]
\thispagestyle{caption}
\includegraphics[width=\textwidth]{#1}%
\end{figure}
\begin{figure}[tp]
\hspace*{-\marginparwidth}\includegraphics[height=0.9\textheight]{#2}
\end{figure}
}
\newcommand\lorem{Fusce adipiscing justo nec ante. Nullam in enim.
Pellentesque felis orci, sagittis ac, malesuada et, facilisis in,
ligula. Nunc non magna sit amet mi aliquam dictum. In mi. Curabitur
sollicitudin justo sed quam et quadd. \par}
\usepackage{graphicx}
\usepackage{lipsum}
\graphicspath{{chapters/}}
\renewcommand{\topfraction}{.95}
\renewcommand{\bottomfraction}{.7}
\renewcommand{\textfraction}{.04}
\renewcommand{\floatpagefraction}{.92} % have a high one don't encourage it
\setcounter{topnumber}{1}
\setcounter{bottomnumber}{0}
\setcounter{totalnumber}{3}
\begin{document}
\doubletakeimage{matron}{stuartpearson}
\lipsum[1-4]
\doubletakeimage{matron}{stuartpearson}
\lipsum[1-4]
\end{document}
Any suggestions to alternatives and improvements in the coding are welcomed and appreciated.
twocolumn, but shipping out two pages at once. That way you have full control over the positioning of floating figures and their captions on both pages of a spread. I could cook up an answer, but it would be a lot of work, so I'd need some indication that (a) this would really be useful and (b) there is no easier, satisfactory way... – Stephan Lehmke May 02 '12 at 15:17ps@captionyou already in the output routine and you also knowthepagereliably, as well as the section marks. Of course via the output routine one need not use any fancy "double image" macros. My caveats are to set the floating limits properly on the left page and reset them later. For example you do not want to end with two images there. On the other hand a solution using the output routine will be more elegant. – yannisl May 02 '12 at 19:03