If something is worth flagging, context isn't needed. If something has problems that can be adequately addressed by adding context, that's what comments, an not flagging, are for. "Flagging with context" is not understanding the purpose of flagging.
There are many modes and methods for interacting. I, personally, am not fond of the dragonwriter method. I'm sure it has its place, but it's just not for me.
Also, you're holding it wrong.