@PloddingInsight:
I replaced my 1960s house single pane aluminum windows with wood/aluminum clad windows. The comfort of having the new windows was well worth it, IMO. I did a hybrid approach with buying windows from my own dealer, hiring someone to install some of the windows first then I finished the rest myself, and then completely hiring out the stucco repair.
My house also had stucco exterior, but did not have the deep bullnose. In my area where there is a lot of adobe style houses with this detail and the window replacement costs might be 50/50 labor/windows split, or even 60/40. Some of the more expensive window companies (e.g. Sierra Pacific) make deep exterior casings/trim that help push that out so there is less of a inset.
If you were to DIY, here is the order I would tackle the problem
1) Detail every window you are replacing size and type (i.e. double hung, casement, glider etc.). Understand the window opening sizes as best as you can. This may involve some demo around one window to find the dimensions of the frame opening.
2) After figuring out the frame opening, you have two approaches:
a) Custom size every window to the rough opening (i.e. if RO is 48" x 48" make sure the new window is set for a RO of 48" x48" - usually this means the actual dimension of the window is 47.5" x 47.5"). .
b) Go with standard sizes and shrink the RO by adding filler framing. I took this approach as it was faster and cheaper. Out of 10 windows I replace, I dropped the sill plate 2 ft on three windows (for egress rules) and only widened one window from 4' to 7'. Definitely dropping was way easier. The enlargement of the window was intense with the framing, but doable. On all other windows that were not being widened the standard width was such that I just had to add a 2x4 inside the jack stud to fill it in.
3) Figure out what you want to do with window sills. Either order them with the window or figure out how they will be built after the window is installed. This is way easier to figure out before moving forward than afterwards.
4) After windows are ordered acquire the necessary tools/material
a) Cutting out existing exterior: I found the expensive diamond cutting wheels for angle grinders to be work the best. The cheap did not do as well. It is possible you have a lath hanging out behind there so expect sparks.
b) flashing - I bought this Dupont flashing that stretches for the sill plate corners. It goes in before the window goes in. I bought the standard flashing (from Home Depot) for the sides and top.
c) Non-silicone sealer, I preferred latex.
d) Nails or screws for the nail flange. The window installation manual will specify the size.
e) shims (plastic works well). There are all kinds of different types.
f) If you are going to replace the exterior you will need all the material for lath, grey coat, and finishing. I hired this out, but if you want to do it yourself it might be wise to practice on a dummy window and wall.
5) When windows arrive, it is time for the install!
a) Cut exterior back 6" from opening. Using the cutting wheel with a chalk line makes this easy.
b) deal with any framing required for window or window sill. This includes any new exterior sheathing. My house had 1/2 board that may or may not have had asbestos.
c) put in sill flashing first
d) slide window in and shim to level.
e) follow directions in installation manual for sealing. This usually is a bead of sealant along the inside corner of the nail flange. Then a bead about 0.5" in from the opening. I put the bead on the window and around the opening with the window out.
f) Insert window and screw/nail flange to frame opening
g) Finish flashing the sides, then the top.
Windows are installed and waterproofed!
5) Exterior (this is based on observation from the crew that did this for me)
a) staple two layers of exterior paper (black stuff) to exposed opening
b) nail strips of metal lath around window
c) apply first coat, let dry
d) apply second coat with a fabric mesh, let dry
e) apply final coat
f) spray stucco color/texture/paint
The bullnose turns might take some extra lath material to shape the turn.
When I bought my windows I got quotes from two providers of the same window brand with in a delivery distance (you may only have one). The one closest was about 30% higher in price, which did not include install. I bought from the building supply shop and had the windows delivered, and I found one crew to help with the install. One of my windows took four people to lift and hang. If I had smaller windows this would have been easier. I learned a lot from this crew, and actually installed two windows and a sliding door myself. The directions online for any of these places is a great resource and starting point. I hired two different crews (because of two different years) to do the exterior stucco matching. They did a fantastic job. If I had the time myself I could have done this, but the mixing and the application is a little bit of an art. If your paint is old and discolored it will not match. Because my exterior was recolored before I bought the place it was easy to get them to match it. You might consider repainting/coloring the entire exterior.
And in terms of the 'environment'. While I am horrified at the waste coming from these intense reno projects I take pride in the fact that I am trying to make my house last another 60 years by sprucing up the significant things like windows rather than someone tearing it down to build a brand new house. Ideally I would last another 40 years in this house, but if the next owner shows up sooner and they feel comfortable enough to leave it as is then hopefully over the long run it is way more environmentally friendly than a new home.
And this hybrid approach saved me about 50% total on the windows. I was quoted from one guy about $60k and I replaced 10 windows, a sliding door, and added one window for maybe about $35k. My windows are large, too. Of the 10, 8 were at least 4' or 5' tall and varying between 6 and 8' wide. This included both exterior and interior drywall/plaster patching.