Clarified summary.

This is supposed to be supported actually, there was a regression at some point.

According to
https://www.mediawiki.org/w/index.php?title=Visual_editor/Feedback&oldid=553398#Issues_with_Bold_and_Italics

this seems to be still happening:

When trying to use bold and italics I run into some problems. You should be able to click bold, then type your content then unclick bold. That doesn't work, you need to highlight information and then click bold and somehow choose it from a little menu that appears under the highlighted text. The same thing happens with italics. Integration with ctrl codes would be useful. Ctrl+b for bold ctrl+i for italics.

Confirmed still an issue with current version.

Mass-moving items into VisualEditor product

Mass-move out of "General" to "ContentEditable".

Re-determining as an enhancement rather than a bug (for product flow purposes; we're still going to get to this).

It used to work well in previous release (December 2011), I'm going to handle it in exactly same way - which is creating insertionAnnotations stack.
@James: Can you re-assign to me?