I'm not sure I want to do any challenges (at this time, anyway), but I have discovered I have a liking for making that Connection.
I worked really hard some months ago to get a fellow Wikitreer Connected, and since then have made a few other Connections. (I also worked with Leandra on Connecting Desmond Llewelyn, which was really neat -- she going from one direction, me from the other, and meeting at some point not quite in the middle.)
Probably the easiest was Max Ferguson, who I'd thought would be difficult, but his mother already had a profile and she was Connected, so attaching him to her made that Connection.
My most recent small-c connection trail (because I don't remember if he was already Connected) would be linking Sir William Robert Campion with his grandparents on both sides. I'd been researching a different branch and followed a rabbit or two and ended up adopting WR, then creating his mother to make the attachment to the Brand line and those who came before (goes all the way up to pre-1066 on the Pierrepont line).