Asking for help in the most awkward way possible.
"There we go, off with you then." England shooed away the final owl. He had just finished writing letters (quick, brief ones, he would explain everything later should they accept his proposal) to possibly the only group that could help him infiltrate Hogwarts. Now all that was left were the replies. This was his least favourite part of any plan, the waiting. It made him slightly anxious. It's was late evening, but England did not want to sleep, he wanted to be awake to read the responses.
So he helped himself to a well deserved cup of warm tea, sat down in a comfortable chair, picked up a good book, and started the wait.
It took some time (after all, the owls had to travel some distance. They were not nearly as fast as muggle texts or emails) but eventually, the first two owls came back, carrying a paper not unlike the one he sent out. After reading it, once, twice, and a third time to commit it to memory, he thanked the bird and set a date for the meeting. He then sent the owls out again, holding a note with the time and place on it.
The next few owls that arrived all carried similar messages of acceptance, and England again wrote the time and place on a small piece of paper, rolled it up, and sent the owl off. He was just dozing off in his chair when the final owls flew into his window with a startling slam, scaring England half to death and forcing him to write yet another letter. His hand was getting cramped.
He spent the next few hours trying desperately to fall asleep again, and after some failed attempts, decided to plan for the next week. Mainly everything to do with Hogwarts and how to get his group in without seeming suspicious.
Harry Potter was going into his fifth year, so if he wanted to be close they needed to be with Harry, in that same year. Many of his group appeared too old to be sixteen (as most fifth years were), so some spell would be required to make them younger. Then there was the matter of wands and cloaks and school supplies, all of which could be picked up at Diagon Alley, but fifth years don't usually get new wands, do they? Ahh, he'd make something up. He could always just say their robes don't fit anymore, and that they don't yet have the required school reading, so he didn't give this much though.
Their cover story, though, would be another story. He couldn't say they were part of Beauxbatons or Durmstrang or another school with close ties with Hogwarts, because a school official could easily figure out they were not, in fact, students there. England would have to come up with either a fake school, or use an existing one without much contact (though that would lead to suspicious people wondering why a school that never talked to other schools suddenly entered transfer students, or a particularly intelligent student could notice that their made up school appears nowhere in history). But there were always going to be risks, no matter what plan he could come up with.
All of these problems could be addressed at the meeting, he supposed, for he was starting to feel sleepy.
His dream that night might well have been one of the weirdest he'd ever had.