Framing windows isn't too difficult (and for reference - my background is in IT).
If you put the header directing below the top plate, you don't need the cripple studs. The cripple studs just provide a way to transfer load to the header and to provide additional nailing surface. In the attachment, you can see a 30x40 window being framed. We have two studs next to the window so that we can secure wider trim around it.
Thanks all - you've confirmed my belief that it really shouldn't be too hard with my skill-set. Probably an annoying long weekend framing, measuring, and then working to get the window hung dead square. The framing part looks particularly straightforward, and it annoys me that each of the contractors (with eyes lighting up like dollar-signs) charged a fortune for it. Shouldn't cost me more than $100 in lumber and I already have the tools.
And what is on the outside of that wall? If you are concerned about water tightness - look up some youtube videos on window flashing.
On the other side is a courtyard that's largely composed of parking spaces and people's sheds. I don't care *at all* how it looks since I'll never see it, and judging what else is back there my neighbors won't care much either. Currently there's just drain pipes and plexi - below me is chicken wire (literally) so anything I do will be an improvement, aesthetically.
I will definitely put up window flashing for water tightness - watched a few of Bob Villa's videos and it seems easy enough... membrane, caulk, insulation, caulk, foam, caulk, flashing, caulk. And then caulk. Annoying, but doable.