A diagram is attached of the Programming Skills Challenge Starting Box.
Yes. This allowed as per <PSC1> which is quoted below.
<PSC1> Teams may handle their Robot as many times as they want during a Programming Skills Match.
a. Upon handling the Robot, it must be immediately brought back to a legal starting position
b. If the Robot is possessing any Scoring Object when the Robot is being handled, these Scoring Objects will be removed from the playing field and can no longer be used
No, it does not need to be in a legal Starting Box to handle the Robot. However, if you do handle the Robot, it must immediately be brought into a legal starting position in the Programming Skills Challenge Starting Box.
There are no specific penalties in the challenge, aside from those specified in the general Game Rules.