Replacing Old Windows

pyrogen74

First off, forgive me if this topic is covered elsewhere, I dont know enough about the subject to know what search terms to enter. Here's the problem: I've got a 70-year old house that has become quite a handful (but I am stuck with it - I was young and dumb when I bought it - now I am just a little smarter). I am considering replacing two living room windows, both are about 4' X 8'. I already plan on gutting the interior to studs since I am re-rocking and re-insulating this room and will most likely have to rebuild some damage from water. The framing is not a big deal, but I am hesitant to start the project because I dont have any idea what to do about the exterior siding. I cant afford to re-side the house (I did this when I moved in so its all relatively new and in good shape) and I am wondering, what is the process for taking out the old windows (the new ones can be any size if it makes it easier one way or the other but I would prefer the same size as existing) and putting in the new ones? What do I do about the exterior siding around the windows? I am concerned about waterproofing and matching the siding. I dont have any idea what this project encompasses. Can someone explain (or send me to another thread) what I am up against with this project??
Thanks in advance.

bob the builder

Well what kind of siding do you have. Or more importantly what kind of window trim is on the exterior. Do you want the same 4'x8' windows put back in. If you don't make the exisisting opening smaller you won't need to get any siding to replace...

bob