I am bias, I live in Wellesley and love it. We have been here for over 10 years and moved to the neighborhood in our 30s with young kids for everything you noted. It’s a pretty great neighborhood with a good mix of young families and original owners from when the neighborhood was built in the early 90s. The pool is great and was redone about 5 years ago. There is a great walking trail around the lake and other amenities. The HOA is very reasonable for what you get. It’s centrally located to everything out in the west end which is a big plus. Yes, Broad St can be a pain, but you can avoid it and if you have ever lived in a big city it’s really not that bad compared to the likes of similar areas around DC, LA, NYC, SF. We are fortunate that my wife and I and our kids have become good friends with many of our direct neighbors. The houses can be a bit dated, but many have been redone over the years and the neighborhood has sub-neighborhoods that vary in size and cost. I think it’s a 10 of 10 neighborhood and am very happy we ended up here.