About windows....
I'm of the opinion that the main benefit of replacing old single pane windows with new double pane windows is that the sloppy air leaking fit of the old windows is replaced with new, tight fitting windows.
When you look at the math, it makes sense. The R-value of a single pane of glass is 1. The R-value of a double pane window is about 2. Triple pane can be 3-5. Yes, that's 2-5 times as much, but compare that with the R-value of an insulated wall: at least 13 or more. Since windows tend to represent far less square footage on the building envelop than walls, floors, and especially ceilings, weatherizing dollars are generally most efficiently used in the following order 1) Seal all air leaks 2) Insulate ceiling/attic, 3) Insulate under floor (for crawl spaces or basements), 4) Insulate walls, 5) Replace single pane windows with double pane windows.
The problem with old windows is that sometimes they simply can't be made air tight because they are so deteriorated or cheaply made in the first place. However, I've been gradually taking down the aluminum horizontal slider windows here - which are probably about 45 years old - and replacing the compressed or rotted out weather stripping (like a line of fuzz) with new stuff. Windows that used to rattle in the wind are now quiet. The only problem is that quite often the old weather stripping is corroded into place and it can take a while to free it. And because you have to pull off at least one of the window frame pieces, there's also the risk that the glass will break in the process. But where I have been able to retrofit the windows I am sensing there is less draftiness in the rooms, esp. where the windows used to rattle in their tracks even when closed.
I've already sealed off all the other likely air leaks, as well as insulated the hell out of the attic (up to R30 in most of it), and insulated about 1/2 of the underside of the flooring above the crawl space. Just those steps made a huge difference in energy consumption, comfort, and furnace cycle times.
Eventually I'll get around to replacing the windows with dual pane, but for now I think making them less leaky is the right thing to do.
I've also found that drawing the shades or curtains at night helps to prevent that "cold sink" effect that windows have. I'm debating whether to get some accordion style cellular shades for the bedroom, which ironically is the coldest room in the house, despite having the most attic insulation, floor insulation, and wall insulation. It's an addition and tends to be more exposed to the elements than the rest of the home (three exterior walls) so that might explain some of it. Leaky air ducts might be another cause. I covered them up with foil faced 1" fiberglass insulation years ago but it's possible it needs to be removed, and all the joins re-sealed with woven polyester tape coated with a special mastic for ductwork.