1. Overall - Oak Park
2. Downtown connectivity -- (Copy from TheProf) close between Shaker and Oak Park; both are served by 2 rapid transit lines. Shaker gets my slight nudge because the 2 Rapid Lines serve Shaker so intimately with stops all over; but Oak Park's L trains are more frequent and get to the Loop quicker.
3. Connectivity to surrounding suburban neighborhoods -- (Copy from TheProf except
bolded) Shaker; it's part of the Heights block of Eastern burbs; seamless between lower Cleveland Heights with the grand homes and mansions plus the Lakes. Beachwood, University Hts. and Warrensville, all adjacent, are easily accessible/connected as well.
Oak Park is bordered by Chicago to the east, while the Grosse Pointes are isolated from the suburbs because they are bounded by Lake St. Clair and the city of Detroit
4. Neighborhood vibrancy - Oak Park has a HUGE downtown for a suburbs. Grosse Pointes have three 3-block long business districts along Kercheval which are connected by a trolley bus during the warm months... Shaker is trying to catch up with its new Van Aken District.
5. Cost of living -- (Copy from TheProf) Grosse Pointe and Shaker may be even here.
6. Scenery -- Grosse Pointe (
Lake St. Clair,
not Detroit River) and Shaker (Shaker Lakes, winding leafy streets) have significant natural beauty. Oak Park has leafy streets, but no water.
7. Retail/Dining -- Oak Park in a runaway with its large and vibrant downtown the other 2 can't match, but again the Grosse Pointes have 3 small main streets with wine bars and coffee shops, etc
8. Crime -- I don't know. Oak Park is next to the terrible neighborhood of Austin, and the Grosse Pointes border the terrible far east side of Detroit.
9. Schools -- Shaker and Grosse Pointe have great reputations; Shaker has only slightly faded. Grosse Pointe North high school has faded somewhat due to the decline of the suburb of Harper Woods and more Detroit residents moving to the cheapest and least unique of the Grosse Pointes - Grosse Pointe Woods. I don't know the status of Oak Park.