FWIW, I had a similar experience in CO when we built our house -- we chose a mid-grade vinyl double-paned window instead of the higher-end vinyl-clad wood, and boy was that a mistake. I don't know if it is the temperature extremes, the strong sun, the wind we had, or what, but those windows ended up being my biggest regret. If I were doing it again, I would get a vinyl-clad wood to have the extra rigidity plus the low-maintenance exterior.
I do agree that there are better versions of vinyl that might last better, though. In our current house, we had to replace 20-year-old horrible vinyl windows (so leaky the 3M wrap you put on with a blowdryer would literally billow out). We did clad wood on the first floor (since the first-floor interior is all stain-grade) and some Marvin vinyl windows on the second floor (which has white trim). Almost 10 years out, the upstairs windows seem pretty solid, although we are getting some closing issues with the ones in the bathroom (e.g. not wanting to latch). But we are also in a much less extreme climate here, so I don't know if the windows are better or it's just an easier environment.
The one thing I would do for sure when you replace the windows is double-check and thoroughly insulate the area around the windows themselves -- one reason many windows feel cold/drafty is because the windows are not installed/insulated properly. We went through a LOT of spray-foam when we retrofitted the windows here, and it has significantly improved the livability of the living room (where I used to feel cold air blowing over my head even with the windows shut and the 3M film on).
I don't know if there is much opportunity to get the quotes down. Our recent replacement were ridiculously expensive -- 33 windows, almost all non-standard sizes (some 8' tall and over $1K per window). So we just did it in phases -- the renovated areas during the renovation; then the upstairs with the kids' room; and then we finally bit the bullet on the downstairs main rooms (the unusually-sized ones) with one of our bonuses. But after having total shit windows in 2 of our last three houses, I just wanted them done right so I wouldn't have to worry about them for the next 20-30 years. If you have experience, you can save money by installing them yourselves -- or hire out the install and do the trim yourself (either re-used or make new). That's what we did -- I didn't want to fuck up the windows, so we had pros install those, but we did a second insulation check/top-off and then did the trim.
