I'm currently working on reversing a protector and I'm having a strange issue with comments in the IDA debugger. Basically, I can comment something while debugging and then if I end up having to restart the debugger, the comments don't immediately show up...but if I enter a different type of comment (non-repeatable where i'd already made a repeatable comment or vice-versa), the original comment will appear from before. Is there any way to just get the comments to show up the right way or am I missing something?

Which version of IDA are you using ?
In my opinion you should report this to IDA's support for eventual bug tracking.

I might just do that. I haven't found any information anywhere. It looks like I'm going to have to write a script to collect comments and replace them. Fun.