I have not had an extend a room since my pop up days. Our rule of thumb with it then was we had to be camping at least 3+ days before we put it up. We didn't normally bother with it for weekends. The awning on the popup was a bag style where you had to put down poles and guy lines, so putting up the room actually helped stabilize it. Another thing we had done to it was modify it so we could put clear shower curtains in it to block wind in the late seasons. Somewhere I have a picture of it set up with Christmas lights on it.
Currently I use an E-Z Up Shelter and have screen and hard sides for it.
Aaron