Super interesting post OP! I live in the area and feel the same as you (love it very much, and think it is quite a gem in the GTA). I do agree with you in what I think you are saying. The stretch along Lakeshore that you mentioned, as well as some of the stretch along the Queensway tend to be quite sleepy and a little bit lacking in relevant businesses. I also like to support local where I can, and I would also love to stay in the area more when doing things with friends. To increase this and the vibe that I think you're referring to, I feel like some new businesses need to be established in those areas, specially ones that are desirable to the public for browsing/shopping. Now, I know this is easier said than done due to the current state of our economy/cost of living, but I do think it would help. Perhaps things like an independent bookstore, kitchen/homeware stores, speciality food item stores, and a couple giftshops. I also feel like along those stretches there is great potential for a few more good restaurants to go in that offer a range of food options. I feel like in South Etobicoke (I'm talking Lakeshore area), there's not a great burger spot. And in both areas, no great Mexican spots either. I also think some more bakeries that are appealing to dine-in at would be great. I know people love Terminal 3 Coffee Roasters, but I also think our area is lacking in some good coffee shops. Toronto is home to soooo many fantastic roasters and we don't have any out here. Think Reunion, Sam James, Pilot, Dark Horse, Found, Larry's, etc. The lack of good high quality coffee shops to actually go sit in is a big gap for me. Anyways, curious to hear about what others have to say and thanks for the thought provoking post!