I don’t want to sound too negative, but there are occasions when what you want is almost impossible without a lot of “artificial” tuning of page breaks.
If the callout falls naturally near the bottom of a page, and the figure falls on the following page, moving the figure back one page will probably displace the callout forward.
I would recommend (as far as possible, and depending on the exact size of the figures):
- Place the figures with [t] (or [h] if you must)
- Place the figures as near as possible to the “right” place (differs for [t] and [h])
- Include the figures from separate files with \input, which will make them much easier to move around when you’re doing the final tuning
In my experience, this is a big eater-up of non-available time (:-)
In reply to Jon’s comment, I think this is an inherently difficult problem, because the LaTeX guys are no slouches. You may like to read Frank Mittelbach’s paper.