For me, it’s magic drop. I still can’t do it at all. 
brent stole and suicides.
Still not too great at suicides 
so far suicides…ive only done one ever…
Boing-Boing, I can do it, but it’s not that good. Suicides are the same story. Leg Wrap Trap and Brent Stole I just can’t do at all. 
Trying to get Kwijibo. Cannot get the yo-yo to land on the string when I cross the arms after the trapeze.
2.0 hook
Whatever trick that im trying to learn
Boingy Boing and Ladder Escape.
Freaking split-bottom mount! ;D I remember day after day of pure fury trying to get it to land without landing on the other string, or hitting my finger >:(
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frontstyle boingy, I can do sidestyle/wristmount boingy, but not frontstyle…
I don’t think I’ve learned my hardest trick yet, and I hope I never do! I want yoyoing to stay fun and challenging for a loooong time 
Any whip tricks. My string segments just keep on hugging each other. And if they don’t magically, the loops don’t form.
Out of all the tricks I’ve ever learned, Magic Drop took the most time and was the most frustrating. I still hate it even though I can do it now.
Iron whip took me three days too learn.
3.0 hook
hour glass… still can’t do it… and i moved on to making my own tricks, and all of mine are a lot more complex and flashier. But i still can’t @#$%ing do it!!!
Suicide. For sure.
Guy wrights 3rd trick in I Punched Boxthor in the Catch 22. Still working on it
brent stole T^T and seasick. i can do seasick with opposite hands but not regularly
Back in the day? Double or nothing. I was learning it on a Fireball, though. Circa 1993ish. In the last year or so? Brent Stole, Seasick, and Mickey-style Eli Hops. I’ve got Brent down, i can do Seasick sometimes, and I’m still in awe of Mickey’s Hops. Nate Sutter has Seasick down like whoa, though.