Once I started to update this list, I realized that we actually have accomplished quite a bit. Obviously, we’re not nearly as far along as we wanted to be, but we’ve still made some good progress. Here’s where we stand as of today:
*Repair missing tiles on slate roof (hire professional): Done! There was a bona-fide hole in our roof when we bought this house. As soon as we moved in, we started searching for a contractor to repair our roof. It turns out that most roofers aren’t interested in working on slate roofs, so finding a contractor was more difficult than we had anticipated. Every time it rained or snowed, I felt like crying. But we eventually found a roofer, and as of January, the hole is gone. This fact alone is worth celebrating.
*Repoint side chimney. Repair/install liner if needed (hire professional): In progress. The mason hasn't started repointing yet, but is evaluating the condition of the side chimney. He initially thought that it would just require repointing, but is now thinking that a full rebuild might be needed. He's going to examine it more this week and give us details. If a full rebuild is required, it will change the cost of this project considerably and we might need to go back to the city for another set of approvals. I'm hoping a full rebuild won't be necessary, but it might be. At this point, we’re not certain what work will be required on the liner, either.
*Rebuild rear chimney. Repair/install liner if needed (hire professional): Also in progress, at this very moment. As I type this, the mason and his apprentice are chipping away at our rear chimney and preparing to rebuild it. We also have this awesome piece of construction equipment in our yard for the duration of the project:

*Install flashing on chimneys (hire professional). Outstanding; will happen once other chimney repairs are complete.