If you don't dismiss a vote dialog before you flag a question (say as needing attention), the new dialog overwrites the old one and both are unreadable. Using Safari 4.0.2. The new text is written over the old text, but part of the old text is still visible. It could be that the new dialog box is not as wide as the old one, but since the backgrounds are flat and don't have borders it appears as the text is only partially overwritten.
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Behaviour in Firefox (3.5.1) and Chrome (22.214.171.124)
All combinations of opening the dialogs show correct dialog windows.
In both browsers you can repeatedly open the two dialogs in any order. Whenever the flag dialog is visible and closed first, the vote dialog gets cancelled as well. When the vore dialog is cancelled first, the flag dialog stays open.
One-and-a-halved: On Chrome 2.0, WinXP, it overwrites it, but the flag dialog is white, so the flagging is legible. Hitting cancel on the flag window nukes them both.