Yeah the solution doesn't even try to explain it intuitively.

Worse, they actively confuse the issue by making the warden an adversary and adding another layer of randomness that's just a red herring. Instead imagine they just put their names in alphabetical order so box 1 is Andy, box 2 is Bob, and so on.

First consider if they were randomly ordered buttons and everyone had to press their button. The people can plan out any order of pressing buttons, it doesn't matter because each person has to win their own separate 50 in 100 bet. So this should be intuitive. (1/2)^100 is impossible odds.

The key part is this: "He then looks into the box belonging to the name he just found".

They are picking an order that's based on the arrangement of names in boxes so they are no longer acting independently from the random box-name arrangement. If everybody was assigned some arbitrary starting box, they are not making 100 separate choices anymore they are making 1 collective choice. But it's the same chance! Instead of making 100 separate fairly likely choices, they are making 1 very unlikely choice (that the starting box order they picked is right).

The second key is starting with the box assigned to their own name.

So imagine this problem as a directed graph. Each person's box is a node and the name within is a directed edge to another node. Every node has exactly one edge to it and one edge from it, and the edges are all random. It's incredibly unlikely to be one full circuit though, instead there are little isolated circuits. For example, box 1 could have "Bob" and box 2 could have "Andy" and if anybody else picked box 1 as their starting box they would never find their name, instead finding 25 Bobs and 25 Andys.

By picking their own box, they're guaranteed to be on a circuit that has their name on it and they are excluding all other random arrangements, so Conan getting stuck on an Alex-Bob circuit of 2 is impossible. The only question is if it will take more than 50 steps.

Now imagine you are randomly constructing this directed graph one step at a time. You open box 1 (Andy's box) and randomly put in Conan, open box 3 (Conan's box) and put in Xavier - can't be Conan because you already used that name! Every next step in a chain has an increasing chance of coming back to the beginning. So on the second step there's 99 names left and one of them is Andy, on the third step there's 98 left and one is Andy. The longer the chain, the more likely it is to end and become a circuit. The warden won't be following this process to assign names, but since every step is random it's the same result as any other random way to assign names to boxes.

So the longer the chain the more likely to become a circuit, and the shorter every other circuit has to be, is finally the reason why the win chance is higher than seems possible.

Why it's 30.5% instead of 23% or something else. Well, imagine the first chain being constructed. The chance of it getting longer than 50 is (99/100)(98/99)...(50/51) which works out to 50%. So the first person (Andy) opening his box has a 50% chance that his chain got longer than 50 before it become a circuit - exactly what you'd expect for the first box. But the chance of building the second chain longer than 50 is much smaller because the first one took a lot of names out of the hat, so say first circuit is 25 long, second chain is (74/75)(73/74)... so you'll have to ask a math genius how to estimate that, but intuitively it's much less likely.