[quote name='Genocidal']Flair and Undertaker, imo, are the two guys who have the most to lose by coming back to wrestle once they're retired, and I'm pretty sure both of them realize it. Flair as a manager in ROH would be pretty awesome so long as he doesn't end up competing in a match, but I don't think even his name could get any kind of huge expansion for the company -- assuming they want it.[/QUOTE]
Flair as a manager in ROH would be a huge step down for him - I think that at most, they'd use him in a Foley-esque role where he's just there to put over new guys on the mic. Flair's already come out of retirement a couple of times, but given the massive send-off for his most recent one, it would be seem like a huge insult to have Flair come back for a match.
More on Flair's departure, and info about Mick Foley possibly leaving after Summerslam because his contract will be up -
http://www.prowrestling.net/artman/publish/powellsblog/article1002329.shtml
There was a similar deal with JBL when he became a commentator, and his deal expired pretty soon after becoming one - he was re-signed quickly, and I'd expect that to happen here, especially after that fantastic promo on SD that showed he can put guys over in a somewhat active role while still acting as a commentator.
Some of my favorite Summerslam highlights -
1991: Bret winning the IC belt, the wedding reception being interrupted by Roberts, the Mountie going to jail, flipping off the cops, and being propositioned by a guy who loves the way leather feels against his body, and Ricky Steamboat selling a beating by the Warlord by trying to crawl up the Warlord and strike him with feeble blows are my highlights.
1992: LOD entrance with motorcycles, Heenan mocking Rocko, DiBiase rocking an awesome white/gold version of his outfit, the Natural Disasters doing a fantastic job of playing the Rock 'n Roll Express against the Beverly Brothers, everything involving Savage/Warrior and Hennig/Flair, and the Bulldog/Bret match ruled.
1994: Blayze/Nakano opened my eyes to how great women's wrestling could be, and Razor regaining the IC belt was cool.
1995: HBK/Razor II was fantastic, Diesel doing a plancha on Mabel, and Horrowitz pimping HIS NEW T-SHIRT were my favorite parts of this show. Hakushi-Kid was good stuff, but not very memorable.
1998: The Venis/Brown opener made me realize how good D'Lo was, Rock/HHH in a ladder match made it clear that they were both going to be big stars in the future, while Austin/Taker had 'Taker do a legdrop off the top through an announce table on Austin that was pretty damn amazing given his size.
1999: The Lion's Den match was pretty good, and the Jarrett PPV opener served as a foreshadowing of every TNA PPV main event ending forever.
2000: Benoit/Jericho was fantastic, Shane's big dive was memorable, and the main event was fantastic despite Angle being knocked loopy right when it started.
2002: PURE SPORTS BUILD! with Brock and the Rock led to their fantastic match, which, like Flair vs. Sting in '88 basically made a guy an instant main event attraction in one night. HBK's comeback was amazing, as he didn't appear to lose a step after a long layoff. Rey/Angle was a fantastic opener that showed that Angle could wrestle anyone, regardless of size, and have a great match with them. Jericho/Flair was great, as was Edge/Eddie - the show was basically wally-to-wall great matches with the only exception coming to mind being Test/Taker, and I don't recall anything bad about the match.
2003: Hunter killing Goldberg in the Chamber despite the fans wanting to see him win the title there, and Hunter being so injured that he could barely do anything in the ring.
2005: Like the 2002 Summerslam, this was a pretty great show from start to finish - Benoit beatng Jordan quickly was great fun, Hogan/HBK was a testament to the greatness of Michaels and his wacky boot sell is the stuff of legend. The Eddie/Rey ladder match somehow managed to be great despite a ton of shit getting

ed up, including a sunset flip powerbomb. Orton/'Taker was good, and Jericho/Cena was fantastic, although I'm not quite sure if it was better than their match the next night.