Thanks for the compliment. When I have time to kill I genuinely enjoy writing, so I don’t mind occasionally posting an article or an involve post here and there.
On the other note:
Compilers and library implementations have bugs, issues, limitations and idiosyncrasies like any other software.
I.E. for years now the standard library coming with visual studio has a flawed chrono implementation that make the high frequency clock pointless as it doesn’t use the appropriate system facilities, rendering it non-precise, possibly non-steady, and with an incredibly uncertain overhead, basically everything an HF clock shouldn’t be 
Thankfully it will be fixed in VS2015 (already is in the tech preview I think).
In your case iterator debugging, like quite a few other VC specific variables, is proprietary to VC.
I also bumped into a related issue with boost some time ago that came down to an actual bug in VC10. It was a while ago, but from a quick search I think it was this:
https://connect.microsoft.com/VisualStudio/feedback/details/640602/vs2010-debugger-watching-std-string-with-iterator-debug-level-0-does-not-work
Also remember that there is a considerable difference between debug and release modes, debug has a lot of added symbols and guards, and it’s possible to see odd behaviours in release that didn’t even error in debug (especially with race conditions), and, a lot more rarely, the other way around.
If your software works with a debugging flag on, but not with the same off, I would be seriously concerned and would look further into it. It’s possible one of the debug guards such a range check is the only thing standing between you and some killer undefined behavior causing your bug. Have you actually tried turning it off and running it in debug mode? VS’s debugger, for all the evils of MS, is actually pretty damn good.
You can find bug reports on msdn.
While it’s usually safe to assume you are doing something wrong rather than the compiler when you’re not an extremely knowledgeable expert of the platform (I make that assumption myself, especially on Windows), if something is really non-sensical and persistent for a long time DO start looking for bugs in the API or the compiler. Some times they do happen, and some are pretty big. I have wasted hours to days some times because of obscure bugs that ended up being in Maya or in VC. Less so on GCC.