I played some more of Nancy Drew: Secret of the Old Clock this morning. Here's what I discovered:
1. You do NOT have to ask Jane to sew the dress. Hooray, a minor timesaver!
2. After doing the pie puzzle, you have to go back inside and get the picture from Jane's podium. Go out the front door and immediately go back inside to have Jane reappear.
3. In order to ask Topham for the Shakespeare book, you have to read all pages of Josiah's journal (after using the trivet to open it)
4. You need to spy on Topham in the hidden tunnel, before you can break into his house and steal the Shakespeare book.
So, not much to say. You pretty much do this portion of the game, as the game designers intended. I've got a few more things to check, but I'm fairly sure. I have the route down. Now that I've been posting about it for two solid weeks, you understand how speedruns can be tough to route, right?