I had so much trouble with Hobbe Juggler. No matter what I did, I could not fling the hobbe a second time quick enough.
I finally found a decent place to get it, though.
Not long after you cross the toll bridge (getting A Job For Life), you will have to rescue Benny the Fortune Teller. During the battle, there is a hobbe with a crossbow in a tree (he's all alone onscreen). Use push and fling him upward. Since he's up in the tree, you have plenty of time to grab him again with push and fling him again.