One way to accomplish this is to use pgfmathdeclarerandomlist{<list name>}{{order 1}{order 2}...{order 24}} to specify all the possible combinations of the pictures, and then use \pgfmathrandomitem to randomly pick one of these and use that as the order of the pictures.
The images are placed in a table with \TableRow{<scale>}, where the <scale> specifies the scale to be applied to the images in that row.

Notes:
- To increase the spacing between the rows you can include a size at the end of each row. For example:
\\[0.3cm].
Further Enhancements:
- The array of possible combinations should be auto generated.
Code:
For this to work I saved the images as 1.png, 2.png, 3.png, 4.png in the directory where I had this .tex file.
\documentclass{article}
\usepackage{graphicx}
\usepackage{xstring}
\usepackage{pgf}
% All possible combination of pictures
% Listed here in increasing numerical order for convenience
\pgfmathdeclarerandomlist{MyRandomList}{%
{1234} {2134} {3124} {4123}
{1243} {2143} {3142} {4132}
{1324} {2314} {3214} {4213}
{1342} {2341} {3241} {4232}
{1423} {2413} {3412} {4312}
{1432} {2431} {3421} {4321}
}
\newcommand{\MaxWidth}{2.0}% width in cm
\newcommand{\MaxHeight}{2.0}% height in cm
\newcommand{\MyIncludeGraphics}[3]{% #1= scale
\pgfmathsetmacro{\Width}{#1\MaxWidth}%
\pgfmathsetmacro{\Height}{#1*\MaxHeight}%
\StrChar{#2}{#3}[\FigureToInclude]% Extract digit from the 4 digit random number
\includegraphics[width=\Width cm, height=\Height cm]{\FigureToInclude}%
}%
\newcommand*{\TableRow}[1]{%
\pgfmathrandomitem{\RamdomMemberOfList}{MyRandomList}
\xdef\OrderOfPictures{\RamdomMemberOfList}
\MyIncludeGraphics{#1}{\OrderOfPictures}{1} &
\MyIncludeGraphics{#1}{\OrderOfPictures}{2} &
\MyIncludeGraphics{#1}{\OrderOfPictures}{3} &
\MyIncludeGraphics{#1}{\OrderOfPictures}{4}
}%
\begin{document}
\begin{tabular}{c c c c}
\TableRow{1.0}\
\TableRow{0.8}\
\TableRow{0.6}\
\TableRow{0.4}\
\TableRow{0.3}\
\TableRow{0.2}\
\TableRow{0.1}\
\end{tabular}
\end{document}