#1: The Town of York

It looks like Horatio scribbled some stuff on this page...

"Our story begins with dear old Mr. Elmsley, who is roaming about in the Town of York, back in 1801. Mr. Elmsley is on a mission to gather signatures for his petition to enlarge the town. Little did Mr. Elmsley know, but only 4 years earlier, Mr. Smith was on the exact same mission. And so, in their own times, both men begin their journeys at the spot where Toronto Street intersects with Market Street. Walking north, they stop at the second house to their left. The owner is present and he is willing to sign his last initial on the petition.
"Just as Mr. Smith did before him, Mr. Elmsley then walks north all the way up to Hospital Street. Walking west on the south part of that street, he finally finds someone is home at lot number 8 in the second block he passes.
"Mr. Elmsley spends the day pacing about the town and collects plenty of initials. He finds that one of the most memorable, perhaps, is the Roman individual living on the North-West corner of King and Bay. He remembered that person in particular, due to the uselessness of his signature, since he signed the house number rather than his name.
"Alas, after a long day of collecting signatures, Mr. Elmsley accomplishes the thing Mr. Smith did not. By putting his own initial on the petition, Mr. Elmsley finally had enough signatures to have the petition go through. This small town will become the magnificent city you live in today, dear grandson!"

David was a good storyteller. This bright morning, exactly 50 years after Elmsley first embarked on his mission, was the first time David told this story to his grandson, Sandford. David also told his grandson about his passion for this city, and asked Sandford to survey the city for him, marking down the things that have changed since Elmsley's petition went through. Equipping Sandford with an old map, David asked his grandson to mark down the changes of half a century.
And so, Sandford set out on his journey, exiting his Grandfather David's house through the north-facing exit, and walking east. He passed 5 major streets, not counting the one where he started his journey, stopping at the 6th. He jotted down the initial of the street he stopped on, noticing that it was named differently than the same street on the old map in his hands. In fact, now that he was looking at the old map he realized he missed an important landmark...
So he retraced his steps, going past a single major intersection, and arrived at the small street that caught his attention. He decided it was important to note this name, since the same name belonged to an altogether different street in his Grandfather's days. Thus, he wrote down the street's initial, so as not to forget.
Having noted this, he now went back to his original route, returning to the first intersection he noted down. This time, he turned northbound, without having crossed to the east side of the street, until he reached the second major intersection on his side. He marvelled at how much the city has changed, while remaining on this street that was close to never touching any royalty. He noted this street's initial, as well. He decided to follow this street west to see what other developments he may learn about. Lo and behold, the final piece of the puzzle fell into place just as he arrived at the third major street, possibly the most important one. Writing down his finding, he felt his work was complete. He returned home to report to his Grandfather.