I have two sets of friends who've lived there for years, one couple for almost thirty years. Both in the Benson View Road/Benson View Blvd. ("Lookout"?) area. Very good neighbours in the general Bension View area, at least from what my "elderly couple" friends who've been there forever say. I get confused between the two, but one is waaay up the hill, so if I were looking to buy there, one consideration would be road conditions in the winter on a road that's steep and winding in some places and rarely plowed or sanded in bad snow events, because Nanaimo is not particularly prepared for coping with heavy snow. I'm not faulting the City--huge dumps of snow are so rare around here that it simply doesn't make financial sense to make big investments in a large amount of snow clearing equipment, or in contracts with private companies to do so. And "Island snow" is completely different (wet, heavy, and more dangerous to drive in) than "interior snow", which is way dryer. I had to adjust when we moved here.
Another road consideration is to avoid the road/s leading to Westwood Lake, a favourite beach in the summer. Although they try to control it, the RCMP can't be there all the time, and it can sometimes get noisy at night in the summer. Not that I didn't help to contribute to the noise myself in my younger days, doing a little illegal midnight dipping.

Only thing that saved us from a "talking to" from the police once was that when they arrived, they discovered that among the group was Frank Ney, mayor of Nanaimo at the time. And the fact that it really
wasn't us, it was a group of teens in the bush. That's my story and I'm stickin' to it.
The closest school might be Nanaimo District Secondary School, which has the added feature of the Nanaimo Aquatic Centre which is basically built right onto the school itself. Pool, water slide, gym, all the bells and whistles. And across a side street from NDSS and the Aquatic Centre is the Ice Centre, two sheets of ice.
Haven't been there for years, but the Jinglepot Pub in the Westwood area, when I've been there, was very nice & friendly. No drunk punks.
If your daughter is firm about which school she wants to attend, I would really, really check whether or not the school has room for her. In order for her to attend a school outside your catchment area (determined by where you live) you will need permission from the superintendent of the school ditrict, probably done via the principal of the school, and then you'll be responsible for getting her there and back. While there's probably city bus service available in the Westwood area, the schedule might not be a good fit for her to use a city bus back and forth to school. There are still parts of Jingle Pot Road, which is the main "service" road for the Westwood area, which are still rural and wooded, and very honestly I wouldn't put a teen daughter of mine out there alone waiting for a city bus, or walking home in the dark from the nearest bus stop. Not that it's any more dangerous than any other place, but I'm super-cautious and I wouldn't have a teen girl standing waiting for a bus in an isolated area at times when it may be dark and with little traffic going by. Or a boy, either.
Another consideration: if you look at an older house, make sure that it has city water service. The Westwood area is on what's considered the "dry side" of the Millstone Valley, so there
might be the unlikely possibility of getting your water from a well. If so, get a copy of the drilling report done when the well was drilled. And check the quality of the water. Some of the wells in that area produce what we called "sulphur" water, and it stinks. Puts rust stains on your clothes while doing laundry, too, if you're not careful. I owned on the other, "wet," side of the valley, and one of the big selling points was a copy of the drilling report on the well, showing that we were pumping from a source with about as much water as one of the Great Lakes. Plus a recent copy of an analysis of the purity of our water. My place sold in two weeks, in comparison with a fairly near neighbour with an inadequate number of gallons per minute, and stinky water with questionable purity. That house was on the market for nearly a year before it sold.
Dover is some distance from the Westwood area and is very crowded. Opened in 1992 and almost from the beginning wasn't big enough, so now what I remember as playing fields when I taught there is partly covered with portables. They didn't sufficiently anticipate the amount of growth that happened rapidly. But right from the opening of Dover, we knew that parents were lying when giving home addresses, using the names and addresses of kids' grandparents who lived in the catchment area, while the kids' parent didn't. People would do anything to get their kids into Dover when, in fact, the only "better" thing about Dover was probably that it was a brand new school, and there's a "snob" value at work there because it's in the north end. Ridiculous. There are excellent teachers in every school, and there are bad ones, too. Every school has its equal share of both.
Wellington Secondary has a "jazz academy" which gives students extra emphasis and time in music and is well-recognized for its excellence. I don't know how they manage it, but students do extra music but still fulfill all their academic requirements. Students are required to apply to attend, and the last I knew, there are fees charged for being enrolled in the jazz academy, as there are for other "academies" offering concentrated instruction in other subject areas.
You've probably already done this, but if not, try
www.sd68.bc.ca which is the school district's website and gives links to the websites of the various schools. If there are particular music teachers or principals at any of those schools whom you want to contact, PM me and I'll give it a shot at giving you their school-based e-mail addresses.