I think Kevin is capable of planning: he just won't do it unless it's something HE wants. He got to the furry conventions and signed up for booths for the tranch fine, he can do the same for England.
He's more capable than he appears but more importantly, he's more capable than he wants to be. Ideally mom plans most of his important things for the whole week, BUUUT if he HAS to he GUESSES he can """"adult""""... Him being underestimate on competence is what he wants, means people think he's a dumb bimbo and he doesn't have to do anything.
Really, thinking of him as more capable than he appears is both true and insulting. "You're able bodied and have planning abilities, why haven't you done X yet?" Is a question that would send him into a big huffy stress sigh as he TEDIOUSLY and STRENUOUSLY explains his position on work and how he can't due to muh mentals. Ask him questions like that his mom would and he'd be upset for about 2 to 7 days later about it.
Kevin should be grateful that she tolerates that he sits upon this earth. She's too kind to even tell him to amundo himself.
Former? Possible. Later? HIGHLY doubt it, as this is way past the illegality of lobotomies.
Really it has about a 20% chance of people succeeding to convince Kevin he isn't a woman and should not get amhole. He's incredibly stubborn and coomer committed. The only thing that might change his mind is having his dick back.
Down here, we all have holes!