Lotta interesting points. I agree with the sentiment that Angle vs Flair today doesn't need to happen, Flair should be using his character and his skills on the mic to help get younger guys over, guys who can legitimately main event vs Kurt Angle.
Angle and Flair wrestled twice on RAW, in July of 2005 and Jan of 2006. Both matches were VERY good, the first one slightly better.
Flair in his prime was out of sight. Watch him against Barry Whyndam in some of their matches from their 87 series, great stuff. No doubt he could hold an audience for long matches. Also watch some of his stuff from 84-85 vs Kerry Von Erich and see how good he makes him look despite his drug problems. Catch Starrcade 88 vs Lex Luger for another great match, Luger has long been an Internet Community punch line for poor in ring performance despite being pretty popular in his heyday. He looks like almost as good as Ricky Steamboat in this match against Flair, credit to Flair's ability to make matches entertaining despite the limiations of his opponent. Flair also wrestled a wide style of match, easily adjusting from the technical wrestling style needed to battle say Bob Backlund, the slower, grinding brawling style of Harley Race, the fast paced move/counter move style of Steamboat and Savage, to the hard core bloody brutality of cage matches vs Dusty Rhodes. Flair was a great showman, great on the mic, and he could convincingly adapt to many different styles of match. Flair was "hard core" before such a term existed, even though his legacy was built on his ability to carry lesser talents to great matches without gimmicks like cages or NO DQ rules, ala Luger and Von Erich.
Someone mentioned the idea that Angle vs Flair today might not be bad because Flair "hung in there" two years ago with HBK. At Flair's age two years makes a huge difference. There was a big difference watching Flair in 1999-2000 in WCW vs 2002-03 in WWE vs 2007-08. Granted, Flair had some pretty good matches during his final WWE run, his WM match with Taker in 02, his SS match vs Jericho in 02, matches with HHH and HBK in 03, matches with Christian, HHH, and Angle in 05, he carried Carlito in 05 and 06, and looked good in matches vs Edge (TLC Jan 06 RAW) and Foley (SS 2006 I Quit Match) but he wasn't nearly as good as he was in his 80's heday, or even when he was in his mid 40's and wrestling very good matches against guys like Sting, Savage, and Eddie Guerrero on Monday Nitro.
For my money, Flair is the better pro wrestler than Angle in their primes though it is close. The idea that Flair in his prime if he were competing today couldn't win a world title is ludicrous. HBK and HHH practically built their careers copying him, if the imitations were winning titles what do you think the original would do ? On WWE's current roster you would have a hard time finding 5 guys who could entertain and work as hard or as well as Flair in his heyday, and the only guys there now that could keep up would be HHH, Edge, Orton, maybe Cena, Taker. Not much else. Plus, these are the guys who win the titles, Flair would have fit right in.
I hope Flair stays as mgr and avoids full fledged in ring matches, it's just not what TNA needs. Fans are not interested in seeing Flair look bad, especially if he's going to lose (notice his match with Abyss, admittedly pre taped, didn;t draw. Fans aren't interested in seeing Flair lumber out there as an old man and be humiliated). However, I don't think at this stage fans are clamoring for Flair to beat all the top guys, it just gets a little ridiculous thinking a 61 yr old man could take on guys half his age and win. It's a No WIn for Flair and TNA, keep him as an on air talent, manager, adviser, etc. His character draws interest, his mic work is exceptional, and he can still take the occassional big bump to jump start the crowd at big shows. Leave it at that, that's what's best for his legacy, and for TNA