haven't you worked on documents secuentially?
Why do you keep many windows open then?
I don't think that I have ever, in all my 28 years of using a windowed operating system, worked on more than 2 documents sequentially in the manner that you describe. I simply cannot imagine the circumstance that would make that necessary. I have needed to make a few changes sequentially to documents (usually image files), but that simply involved opening them, making the changes to each and then closing it.
So why do I keep many windows open? Because web development involves many different things. For example, I will be working on a .php file, and will have several other .php files open for reference to the functions or other code contained in them. I will also usually have a browser window open with some PHP documentation. I also may have a .css file or two open. I also may have some MySQL documentation and phpMyAdmin open in a couple other tabs in my browser. I arrange everything on the screen so that I can see the ones I'm using most frequently together, and usually use either Exposé or a simple click (if I can see the window) to quickly switch between windows.
If I need to switch back and forth frequently between two windows that fill the screen, then I will use command-` or command-tab (depending on context). In that circumstance, I have only ever needed to switch between two windows, and I absolutely, 100% expect command-` to give me the next window in the stack, not whatever the next window in the stack was ten minutes ago before I moved things around.
In my experience with user support, what I do is far more sophisticated than the average user, but on the same lines as what they do. They may have several spreadsheets open for reference with QuickBooks while doing billing. They may have a calendar app and a web browser and a customer database while doing scheduling. I've never seen any end-user need to repeatedly cycle through a virtual "stack" of documents as you describe, touching each one in turn and then cycling back to the beginning to start over. Honestly, if you need to repeatedly cycle through 5 documents sequentially, you're doing something that would be better done by a machine. Figure out how to automate that task.
Currently the history is REPEATING the same doc. So if you history is 1,2,3,2,1,2,3,2,1,2,1,2,4,5, you'd need 14 keystrokes to get doc 5! And you only have 5 docs! Do you think that's right?
That is not how it works. (Of course, you keep bringing Chrome tabs into this, which has nothing whatsoever to do with window-cycling behavior on the Mac. Perhaps Chrome does tabs like that, but I don't know, and I'm not addressing that.)
Command-` cycles through the open windows IN ORDER. There is no history. If you have 5 open windows, you will need to press command-` precisely four times to reach the one in the back. If you stop and do something with one of the windows, then the next time you use command-`, you must deal with the current order, not with whatever order the windows had at some unknown time in the past. That is the way it should work, IMHO.