My house is 60 yrs old. Most of the windows are single pane, 20-30 yrs old and are in severe need of replacement. They have all been siliconed shut to avoid leaking due to age and improper installation to begin with. However there are many many things that need to be done to our house and we can afford to do this in stages but not all at once. Our house is a cinderblock house with minimal insulation. We have completely redone most of the living areas of the house but have not touched the exterior. We need all new windows, we want to stucco the outside for exterior appearance and help with insulation of walls, and we need a new roof (probably make it another 3 yrs on roof). We have the best insulation in the attic money can buy so says long fence. I just don't know which one to do first - many different opinions from contractors. I can do maybe one every year or two - with the goal of having it fully complete and remodeled in 4 years. My biggest concern is with the windows since cinderblock is thick and then adding stucco to the outside will add to the thickness. If I replace the windows now - how will it fit/look when the exterior is redone? Would I be looking at replacing these windows or having to do a not so ideal work-around on the exterior to make the appearance look nice? Should the thickness of the walls be a factor when selecting windows? What should I look/ask for? Also if I absolutely should do the stucco first, shouldn't the roof be redone first so as not to damage stucco and allow seamless appearance? I'm looking for any recommendations / suggestions from those with exp with old/cinder block homes and experts. Greatly appreciate any advice!! Also I've been looking at Anderson windows b/c that is what I've always had - any recommendations?

PS for other remodel projects in our house we have gone with the local contractors recommendations...needless to say we are no longer using several as I believe their suggestion/recommendation have been based solely on what solution will put most money in their pocket at that time. We've had to redo many many things b/c we didn't go with our gut and went with contractor recommendations which has cost us thousands and thousands of $$$. so I really appreciate the advice!!!