Mike Stall has had a recent string of posts about debugger features, which got me thinking about what I waste time doing in debuggers these days.
Omniscient debuggers would be great, but what I would really like is a memory window that I can annotate. I don't care if this makes it into Visual Studio or WinDbg, but it would save me time that I currently waste scribbling on notepads.
I should be able to stick some comments in the memory window, and they should stay at that address for the extent of the debugger run. This is what I mean:

In this case, since my memory window is @ESP, I should be able to see my annotations being pushed down on the stack as I step.
I realize maybe one percent of developers could use this, but dammit, we're the coolest one percent.
Yeah, I think that’s basically it. In this case I was trying to keep track of parameters to a function call on the stack.
I suppose the concept is somewhat related to the “object ID’s” in VS2005. Maybe it’s a more generic version of that (or maybe your next move is to tell me there’s a way to make object ID’s do this).
Addendum: I should perhaps mention that this kind of thing is allowed in programs like the IDA disassembler and OllyDbg. Unfortunatly the former isn’t really a debugger and the latter isn’t as familiar or useful (to me) as VS or WinDbg.
This sounds very related to letting you create your own custom symbols? Does this request just boil down to:
1) the ability to associate arbitrary user comments (perhaps just plain text strings) with an arbitrary address? (really just a {addr,name} pair)
2) a decent UI to input + visualize this?