A couple comments from this guys perspective, of the ones I've played.
Franklin Hills - Is a wonderful Ross course, but it has been pointed it that it's not only a "Jewish" club, but one that is quite exclusive. It has been mentioned that it "flys under the radar, and thats the way they like it" that couldn't be more true. Cross that off your list.
CCD - I grew up in Grosse Pointe, my parents still live there, I've played Oakland Hills and Franklin Hills and still have not had the pleasure to play here. It's a very blue blooded membership, a lot of old money and equally as exclusive as Oakland / Franklin. Cross that off the list. A close friend recently told me that the health of the greens has and is a VERY SERIOUS ISSUE, BUYER BEWARE.
DGC - Although I know many locals who absolutely love this place, I was very unwhelmed. I played the "championship" course, and felt that it had lost a lot of original design intent when they tried to stretch it and It just seemed like the course wasn't comfortable in it's own skin if that makes sense (I'm sure it doesn't) I've heard good things about it's sister course, but can't comment. My parents are members at Lochmoor in Grosse Pointe, and I couldn't believe there was a course in the area as FLAT, but alas DGC was every bit of that. Wouldn't recommend.
Lochmoor Club - Like I said, my parents are members and I grew up playing here. A very tight, tree lined (too death!!! in need of some major cut-back) but usually in good shape. Very flat. Greens are small and rather dull for the most part, but a good membership and I understand they are offering some great deals, particularly if you're under 30. If your brother is married with kids they have an excellent swim program and great tennis / workout facilities. Its also very close to Wayne State and in a wonderful neighboorhood. They've recently paid off all of there outstanding debt, which in these times, is a definite PLUS!!!!!
Birmingham CC - I really like this golf course a lot. Plenty of elevation, good conditioning and fairly interesting putting surfaces. Would definitely reccomend from a pure golf standpoint.
Plum Hollow - I pretty sure I played here in the Buick Scramble several years back, remember enjoying it. I think they were really cutting back some trees, but I think that had more to do with disease than anything.
Red Run - Have not played but have friends who are members. They really like it here, and It's relatively close.
Indianwood - It's not relatively close but the OLD is AWESOME, and so is the clubhouse. I've played once and plan on returning this year. George is right, the NEW is the exact opposite of the old, which albeit maybe a negative to some, variety is also nice, as is the ability to probably land a tee time nearly anytime.
I cannot see Essex in Windsor worth the hassle of crossing International Border (although I hear the golf course is wonderful) and you definitely need a passport now.
My final recommendation is tell your brother to contact these clubs, most of them if not all will have a membership director. HE CAN PROBABLY TOUR / PLAY NEARLY ANY OF THESE CLUBS AT NO COST AND THAT SHOULD DEFINITELY HELP MAKE HIS DECISION (plus if you're in the area you can certainly piggyback!!!!). I don't think pictures, even on this website are adequate enough to make a final decision. Not to mention, once he's in at these clubs, he should have no problem setting up the occasional game / round at most if not all of these other clubs via his head pro. Just my two sense, let me know what he decides. I plan on eventually moving back to the area (doesn't seem so desirable at the moment but hey, there are some great deals to be had on the private side right now) and will be interested to know his impression of the process.
Nev
P.S. LOCATION SHOULD BE A MAJOR FACTOR, GO WITH SOMETHING CLOSE TO HOME.