After Cavendish dies, Dakota goes back in time to save him and sends his alternate timeline self to an island, as they can't both be around at once. It turns out Cavendish has died many times, and there are many versions of Dakota in the island.
Meanwhile, Milo and his friends head to the unveiling of Hamosaur 2 (a replacement for the one that was accidentally destroyed in "Family Vacation"), but Milo can't find his usual shoes, and his bad luck with shoelaces rears its ugly head once more.
Tropes:
- Continuity Nod: All the times that Dakota saved Cavendish from a life-threatening incident are explained.
- Darker and Edgier:
- For a lighthearted series, this is the first to features a lot of onscreen Family-Unfriendly Death, from Cavendish's head blowing up, to falling in lava and leaving behind his skeleton.
- Not to mention the Fridge Horror aspect of Dakota repeatedly uprooting his own life and abandoning EVERYTHING to save Cavendish. The Isle itself gets some laughs, but Dakota's trip to it is treated as being quite sad, and his usual happy-go-lucky nature is all but gone the whole time.
- Death Montage: One featuring the numerous times Cavendish died and Dakaota went back in time to save him.
- Epic Fail: Milo's experiences with shoelaces. A flashback reveals that he once tied himself and Diogee together. He later does the same with his friends.
- Initiation Ceremony: The newest Dakota is made to think he'll be cooked and eaten by masked tribesmen, as a way of being initiated into the fold. One Dakota, however, is openly disappointed they're not actually going to eat the new one.
- Naked People Are Funny: Birthday Suit Dakota.Birthday Suit Dakota: It's my birthday!
Other Dakota: Put on some pants! - Never Shall The Selves Meet: Averted. There's an island full of Dakota's other selves but no harm is caused from them being together.
- Seen It All: Most of the locals are used to Murphy's Law. The Mayor, on the other hand, is 100% done.Mayor: Hi, folks. Welcome to the Fifth Street re-dedication ceremony. We all remember the events of the runaway antique firetruck and the damage it caused here. But as your mayor I'm proud to say we're back! Businesses are open, and... [Notices the crowd looking at something behind him] ...There's something behind me? One of the Murphys? Murphys, yep. Out of control water truck? Giant boulder? No, no... [looks] Oh, yeah! Giant dinosaur-like creature of some kind! Yeah, oh, that's nice! [Hamosaur rips through the ceremony] Yeah, yeah, get that mailbox! Yep. I love being mayor here. I love it! [beat] I LOVE IT! [throws mike on the ground]
- Unseen Character: Birthday Suit Dakota, for obvious reasons.
- What the Heck Is an Aglet?: During a random moment, Milo explains what aglets are (they're shoelace tips). Later on, when it's revealed Milo's loafers are manufactured at the Island of Lost Dakotas, the last Dakota to join is told by the others they don't make shoes with laces because they don't have plastic to make aglets.
