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It might seem simple, but it's not. The DB part is fairly easy (and the hidden flag is already stored in the Color column, along with color, icon, & font info), but the UI is another matter.
Just a few of the things that have to be dealt with
1) allowing flags to be added, removed, and re-ordered.
2) long lists of drop-down menus when it now extends to 20- or 30-some items. A submenu of a submenu is more work as well.
3) the Flag toolbar having to dynamically size to how many are defined in the current DB, and handling switching between DBs which could have different numbers of flags.
4) changes in the UI in many places to handle a variable # of flags.
5) currently, keyboard shortcuts are available (Shift+B for blue, etc.), would have to re-think this to allow more customization and more shortcuts, possibly like what is supported for favorites, but it would become unwieldy to have and need to recall dozens of shortcuts
6) ensuring backward compatibility with existing data
7) optimizations could be necessary to handle 4x as many flags as before without lag.
More like a couple hundred hours than a couple.
Increasing the max supported is not a bad idea, although 32 would be a lot, and it seems as though what you're really after is an importance attribute that would alter the behavior of each flag value. There already is a Priority attribute defined -- I'm thinking a better way to approach this would be to leverage that (or possibly a new Importance attribute), something like:
Be able to configure some properties for each Priority value, via a new dialog, similar to the Flag/Flag properties dialogs
1) Font styling (i.e., bold, italic, underline, etc.)
2) Background color override
3) Label used in submenus
Then add a submenu and keyboard shortcuts, again similar to Flag, to set the Priority item attribute value.
The Priority would then be used in conjunction with the Flag attribute to format the item's font style and background.
I could see a use for that, but it's not so simple to implement either.
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