Meanwhile, I got some good news about insulation, so good that I'm kicking myself for not doing it sooner. It turns out that it will only cost about $1,000 to add R-30 (15 inches) of blown fiberglass insulation to 1,100 square feet of attic (existing is perhaps R-10 to R-15). I was expecting it to cost twice or thrice as much, so I am willing to proceed with just one estimate. Besides, I couldn't get the requisite three estimates -- I called four contractors, two made appointments, and only one bothered to show up. Better yet, I should be able to get a grant for 50% from the Historic Chicago Bungalow Initiative.
The grant for insulation also includes water heaters, so this is probably a good time to go tankless. It will be a lot easier to buy a $950 water heater if only half comes out of my pocket! I'm looking at the Bosch AquaStar 250SX. It's more expensive than some other brands, but it has a better warranty. Plus it has electronic ignition, which saves the cost of burning a pilot light 24-7-365. Considering that our current heater was among the most inefficient when it was new and that tank heaters lose efficiency over time (ours is 11 years old), I should make up the cost pretty quickly. An indirect-fired model using the boiler would be even better, but as I said before, I'm not enthusiastic about paying for a new boiler at the moment.
Window treatments will help, too. I am putting together an order of Symphony honeycomb shades that boast R-4.6 insulating value, higher than other brands (naturally, the company is located in Vermont). They are much cheaper than the Smith+Noble triple honeycombs (which had a lower R-value) that we put in the dining room and master bedroom a few years ago (by the way, I will never order from Smith+Noble again because they are spammers -- I get their promotional e-mails at an address that didn't even exist when I ordered from them, in addition to my regular address). We'll start with the living room, an upstairs bedroom, and the sun room, a total of ten big windows, one picture window, and two little casement windows (too many darn windows in these bungalows!). I'm not going to go all-out with the side tracks, though (except maybe the upstairs bedroom) -- those just wouldn't fit in with the dark-stained oak trim we put in a few years ago. I still need to decide what to do with the dozen or so short basement windows that we never use. I'm half-tempted to stuff fiberglass batting into the window frames, but that would look so white trash.