Being new, I read back through the related threads for some clue as to the overall question. Wanted are a home for boater4life, who's a late-20s guy with a girlfriend. He works Downtown.

Also wanted is a home for his 42-foot power boat. The boat obviously needs to live on Lake St Clair. He would prefer the boat live with him, but that probably cannot happen unless he goes well up the lake to Harrison Township-- a substantial commute from Downtown.

He's been looking at houses/neighborhoods and seems to have narrowed down the ones he's interested in to Birmingham and Grosse Pointe. He can afford "not a starter house" in either location.

Harbor Island in Detroit was mentioned in a prior thread, but I don't think it's at all easy to get a 42-foot power boat in and out of there. Same would be true for nearly all St Clair Shores canal houses.

In addition to access to the boat and to work, he wants to be around people like himself [[other than age range, so far undefined) and to restaurants, shopping and malls-- for something to do during the winter.

Given that our boating season is relatively short, it seems to me that keeping commute time to/from work and boat is key. If boater4life lived in, say, the first 6 or 8 blocks of Grosse Pointe Park and kept the boat at Windmill Pointe Park in GPP [[where there may well be a wait list and there is an annual dockage fee), that would be the optimal solution for maximizing boating time.

The docks at Windmill Point are [[or were last I looked) fairly straightforward-- get on your boat and go. I have known the docks at GPYC to be more social, and I assume the same would be true of the Little Club. They of course cost more and require a small bit more travel time, but may be worth it for him if that's the sort of setting he prefers.

Looking around my GPP neighborhood I'm seeing more and more early-30s couples, often with very young children, moving in. Some of them grew up here, went to other cities or stayed local and bought in Royal Oak, and are now moving back. Given the traditional GPP advantages [[commute to Downtown, schools, parks, water access, like-minded neighbors for the most part) and the increasing attractiveness of the Downtown-Midtown playground I expect that will continue. That means the "others his age" issue will work itself out in short order-- so long as he doesn't mind that they have kids.

As others have mentioned here and in prior threads, there are enough okay-to-great restaurants around. Shopping for things other than food, not so much. Shopping for pleasure [[Somerset type) hardly exists at all.

His current friends live in Oakland County. He could perhaps make some new friends here, or in Downtown/Midtown which are becoming more vibrant daily and are GPP's playground really. Or he could get in his car and go meet his friends in Royal Oak or wherever. Presumably he drives to meet them now.

I think the real deal-breaker could be whether the importance he seems to place on shopping for recreation could mean he and his GF like to dress very fashionably/edgy and/or are very designer brand-name conscious, and that seeing others dressed the same way is important to them. If so, and if they anticipate they'll continue with those preferences going forward, GPP is [[thankfully!) definitely not for them.