One thing that needed to be addressed before the winter turned out to be my largest purchase to date: new windows.
The dilemma: I didn't mind the old original windows, but they were in really terrible shape. They were not entirely beyond help, but they would have required countless hours of work. The old aluminum storm windows were also really bad. Several had broken levers, and would barely open properly. I also had an exceptionally hard time removing the screens. I actually had to practically destroy one of them to get it out (the one in the bedroom that led onto the flat roof of the garage).
Another issue regarding the windows was the fact that all the main floor windows had already been changed just under a year before I bought the house.
I decided that I wanted all the windows to match, and that I'd prefer to have the double hung windows for easy cleaning. The fact that they also don't need painting, and won't rot was nice.
I do realize that they are still "crappy modern vinyl" windows, but I don't regret my decision. I know that the old house purists will curse me, but I did keep the original sashes, and the windows were all plain 1 over 1 (nothing fancy).
These were the new windows after they were delivered. They were surprisingly heavy.
One of the 8 new windows in it's new home:
The two windows in the back porch were the worst of the two. The windows that were there were very thinly framed windows that look like they were recycled from another spot. They almost looked like storm windows.
At this point, the windows were in, but they were not capped on the exterior. I had a friend of my mom's come and do this for me. Here are the finished windows:
The only other window that needed work was the one in the bathroom. The current window was installed in 1992 I believe, and it was from a local lumber supply (actually the same place where I bought the new windows). The window was non-matching to all the other ones, but it was still in good shape so I reused it. I did, however, need to rebuild the entire framing for the window since it had been really poorly done.
For those who are wondering, the room you see beyond the window is the back staircase with the two windows pictured above.
The last detail I did on the interior windows (all the main ones on both floors) was to install a custom-milled detail moulding to hide the seam where the vinyl insert window (and shims) fit into the window opening. On the main floor, they simply covered this with a large bead of caulking. I added the new moulding over top of this.
Here is one of the fully finished, puttied, caulked and repainted windows.