I did get the windows and stormwindows painted, so I've probably got another 3-4 years before I have to do anything. But I'm not painting windows again.
All our new windows are going to have a heavy duty extruded aluminum exterior; pre-painted with a permanent finish! After we finish the addition, we're going to replace all the other windows in the house that were not affected by the new construction. We found a brand that is really nice. It is Eagle windows; the company was started by folks who used to work for Andersen windows. They are extremely well made; SSQ was mightily impressed, and it takes a LOT to do that.