Hello Joey,
You are correct that when you check out one source controlled file, you are not "allowed" to add some "Check Out comments" on it. I think you can consider submitting one feature request on the Microsoft UserVoice site here:
http://visualstudio.uservoice.com/forums/121579-visual-studio
In addition, as we know that every check in produces one changeset. So for your scenario, I think you can consider checking out one file and making some modifications for it and then finally checking it in. At this time you will get one changeset which contains
the comment information.
Thanks.
Vicky Song [MSFT]
MSDN Community Support | Feedback to us
