I don't think this Portland team would be able to beat Clyde's best Blazers team in a seven game series. In fact, I don't think they would win a single game right now.
Buck would shut LMA down, hard. Roy and Clyde would duel with Clyde coming out on top. Porter would absolutely destroy Blake. All of our small forwards put together don't make a single Jerome Kersey. At Center, Duck and our two headed monster would battle to a stand still.
Ainge, Young, and Robinson versus Bayless, Rudy and Outlaw. I would put the former ahead of the later.
Give this current team a few years and the picture might be different. But right now the 1990-1991 Blazer team would bitch slap this current team.
I have to agree that the simulations for the 1990-91 team were a little stinky simply because I couldn't tweak the rotations to match reality. But, I have a little different view of the matchup than you. I think we're pretty close to being equally matched.
1 - Roy is a smarter player than Clyde, and can (as has been shown in his duels against Artest, Melo, and Kobe) basically goad a shooter into taking bad shots. I'm thinking 4th quarter against the Lakers in April 09. He got into a shooter's duel with Kobe, and Kobe started missing first. Clyde had this tendency to match his opponent shot for shot if his opponent was hot, often to the team's detriment. I think Roy could gain an advantage here.
2 - LMA cannot be stopped by Duncan; Buck (at 6-8) is not going to shut him down completely. LMA's game isn't just back-to-the-basket or slashing; he's got midrange, high post moves, and can pass out of a double-team. Buck may shave 5 points off LMA's average, but that still leaves 13-15 points a game.
3 - Rudy and Ainge would be a battle for the ages, but also of the ages; Rudy, being younger, faster, and more athletic, would force Ainge to foul before Rudy could get away for an alley-oop pass or open three pointer.
4 - Robinson and Outlaw would be interesting to see, since I like both players quite a bit. Cliffy gets the advantage here, because Outlaw couldn't guard 17-year-vet Cliffy, let alone 2nd-year greyhound Cliffy. But, at this point, Outlaw has a 3pt shot and Cliff doesn't.
5 - Bayless/Sergio (if we're going 08/09) versus Young is a pure win for Young; he'd pick their pockets so often, they'd start carrying their wallets on a chain for their own protection. Since neither showed much interest in defending the 3, he'd also pound them there.
On the whole, I think if the game stays close, the 1989-93's lineups tended to fold a little under pressure, whereas the 2006-2009 teams have blossomed under that same pressure. If Clyde's teams are to win, it'd have to be by a blowout.