You may be able to script something like that have it triggered by an open event. Each time a document is opened the script would be triggered. Windows tile size will change and all open document would need to be fitted to their new windows size. I would think that would be quite annoying and disruptive. You could also set up a close document event and resize the remaining open documents windows.
If you zoom one image to a particular level you can use Window > Arrange > Match Zoom (Alt+WAZ on Windows) to match the other windows to it.
Not exactly what you want but it may help.
Thanks guys. Scripting might be an option. I might have an old applescript somewhere that finds the dimensions of an image. It would probably still be a lot of work just to skip an annoying step. The Match Zoom was the easiest thing I could find. Sort of a compromise.