If you can bear with these premium graphic artworks.
The current flagging system on questions has 3 or more dialog boxes to be navigated through to close for specific reasons or to use the "other" reason. The close vote dialog boxes have two or more to navigate through.
The UI is also inconsistent. The reasons all start with bold on the first dialog boxes and on the final one, the bold is scattered part way through sentences making them less obvious.
The flags modal has a duplicated duplicate close reason, on two dialog boxes (irony is noted).
We have problems with declining migration flags, as other sites usually don't want our stuff. So I recommend removing those suggestions altogether on flags and keep them only for the close voters, as they've had time to get to know how the site works (well some of them have). There's no real need to have the options for particular sites for migration within the main flag dialog, we could include them when the user selects on "belongs on another stack exchange site" or they could just be typed in, as they so often do for code review and in the comments.
Lastly, the broad and unclear reasons are on the flip side of the same coin, there's no real harm in combining these.
So my proposal is to reduce the number of dialog boxes by 1, by trimming the reasons, and putting the last two boxes into one box and making the format consistent with the use of bold titles.
Please give your suggestions. We may be able to come to a consensus, even if that may be leaving it as it is.
NB out of scope: Personally they're a little wordy and I would think would be improved with shorter reasons, less clutter with a good link in each for usage. Though this is out of the scope of this request.
The current flagging dialogues
1st Flag dialog
2nd Flag dialog - new question (< 60 days)
2nd Flag dialog - older question
3rd Flag dialog - new question (< 60 days)
Why not simplify question flags to two dialog boxes?
1st New flag dialog
I'd recommend Stack Exchange engaged in their own graphic artist.
2nd New flag dialog
Without including the repetition between the flags.