We just came here from Utah, where the per pupil spending is at the bottom of the list, and the teachers are all on the cusp of retirement and burnt out (or fresh out of college), so take my assessment on Bend's relatively wonderful schools with a grain of salt.
Our family is a lot like your description - upper middle, but can't stand hoity-toity (blue collar people that make white collar money), so we moved to the NE side of town near Pilot Butte Middle (for our 7th grader) and Juniper Elementary (3rd grader). We also wanted a 1/4 acre plus on a relatively flat lot, so that ruled out much of the west side with its postage stamp sized lots, and/or a 10 min drive to town from "The Butte" as one snooty lady I know referred to her Awbrey Butte neighborhood just before she climbed into her gold, blingy, Land Cruiser (there's more than one butte here lady!). Walking distance to schools, and parks was also a priority.
At the moment though, my youngest is attending Ensworth, which is the smallest public elementary school in town, and I cannot say enough wonderful things about his teacher (Crumpton) and the principal (Timms) and Linda at the front desk (super organized). We are moving in July to our permanent home a 1/2 mile south, which is in the Juniper boundary and are on the fence about whether to switch schools, since we're such fans of Ensworth.
Juniper is the technology magnet school. iPads for all (or many/most?? not sure). They also host the TAG (Talented and Gifted) program. We just met those teachers, as my youngest is testing for that program, and they seem amazing. A random parent I ran into in the parking lot was raving about Juniper for her kids. The buildings are much older than Ensworth's. I've also heard great things about Ponderosa Elem (also new-ish), Lava Butte Elem and Sky View Middle. I know very little about Mountain View High (nor does anyone I ask it seems), although that's our boundary high school and I'm sure I'll learn more in a year or so.
Pilot Butte Middle has a new IB (International Baccalaureate) program, and so does Bend High. Bend High's principal was recognized as principal of the year, which unfortunately means he's leaving for bigger and better adventures. People want
to live in Bend. Teachers
want to live in Bend, so it seems like they get the cream of the crop here. I have two teacher friends that want to move here, but can't because there are no jobs for them. Most of the teachers I've seen or met, appear to be in their 30's and 40's, which I find to be prime teacher age - experienced, but not burnt out yet.
I guess my point is, the schools here are pretty kick-butt from what I've seen - even those in the statistically lower income areas of Bend. This was one of the top 3 items on our PRO list for our decision to move here.
One last note - they are building one new elementary school in the SE, and one new Middle school on the NW (by Summit High). This is expected to result in significant boundary adjustments, and teacher/administrator movement. I believe that will be a year or two from now. Most of the Bend schools are currently overfull, and it is difficult (sometimes impossible) to attend an out-of-boundary school. That being said, the teacher/pupil ratio is still lower than we had in Utah.