This reading shows you something you may be interested in. The wrapfig package altogether with the subfig are a good suggestions, though you need to put your wrapfigure env before the first paragraph of the page and you must know and "fix" the width of the content, something like
\documentclass{article}
%\usepackage{subfig}
\usepackage{wrapfig}
\begin{document}
\begin{wrapfigure}{r}{.6\textwidth}
%% your content, maybe with \subfloats
\end{wrapfigure}
% the very first text of the "new" page
Lorem ipsum dolor sit amet...
...
\end{document}
The link shows you the example of the gull, where the width of the graphics is a little bit less than the width passed to wrapfig.
The idea behind floating insertions is to free authors from thinking too much about where things go. Usually, you should not be worried about it, unless you are doing something that it is out of the "scope" of (La)TeX, though of course you can do it e.g. writing your own package and playing with LaTeX internals or TeX primitives, or hoping someone else had your same "problem" and wrote something to solve it...
In particular your rightmost second case can't be done with subfigs and wrapfig (or at least, I was not able to do it using these packages).
Reading manuals of the packages may help too (the direct link is to it mirror of ctan, likely you would prefer a different mirror)
wrapfigseems to be the way to go. – Martin Scharrer♦ Jul 16 '11 at 11:45subfigdoesn't work outside normal floats. – Martin Scharrer♦ Jul 16 '11 at 11:54