/THF gives you a free flee to use, and sprinter's shoes + movement speed equipment will get you to the 1st Smile Helper that much faster. I imagine BRD/THF would be decent if you Marzurka before talking to the NPC.
Honestly it wasn't that hard, it was just stupid annoying.
I did West Saruta, Tahrongi, and Rolanberry to get the new items. For the 1st and 2nd challenges, if you have flee still on you can run to the 1st Smile Bringer quick, so if you dont make it in time, start it right after with the boost. The 3rd stage you cant do this, but Rolanberry was cake compared to Saromogue.
I got my HQ hat on my third try, the 2nd running one took me by surprise, but just spamming tab like a madman when I was coming up to them made it easier.