The most common and most likely answer to this crossword clue is the 5 plus 4 letter word SPEED BUMP
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More clues leading to the result SPEED BUMP
Buddy explains!
The straight part
We know that "Over which, e.g., Picasso would proceed cautiously" is the straight/definition part of the clue. The straight part is often a synonym or definition, in this case over which, e.g., picasso would proceed cautiously = speed bump.The cryptic/wordplay part
In cryptic crossword there's often an wordplay/cryptic part as well.This part involves a more complex hint, such as an anagram, homophone, hidden word, etc.
Sadly, We don't have an explanation for this specific crossword clue yet.