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Windows should fit into the rough opening(within an inch or so)...Take off the trim on the inside and measure the width of the opening between the studs (2x4's). The windows' height is govererned by the header above and the framing under....It is easy to make a window a little longer by cutting the wall under (ie: a 36" height window can be replaced by a 45" height by simply cutting 9" deeper and reframing...You can not cut into the header(framing above). It is also much easier to keep the current width or narrower so as not to have to replace the current header...Pack insulation between the window and the rough framing before retrimming...Nailing and caulking instructions are usually on the window...Follow carefully so as to have leak free prooperly insulated and sealed units.
Whether you use two windows or one is a matter of taste, as long as your window air conditioner fits...There are also companies that build windows to fit in your existing frames and you do not have any work at all, in terms of retrimming or sheetrock work.
Home Depot or Lowes carry anderson and pella as well as other brands and usually have step by step instructions for the do-it-yourself-er.
I have replaced many doors and windows (I made all of my windows 54" deep to let more light into my home) and it really is not that difficult...Depending on the size you may need help lifting the windows in and plumbing them(making them square and level) up.
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