Chicago is an awful matchup for us, I'm pretty sure they would beat us again in a playoffs series, as much as I hate to admit it. Their defense always kills us, and even offensively, they somehow execute their plays better than us. Thibodeau knows how to play the Bulls against us and will completely outcoach Kidd. That is the team we should be absolutely looking to avoid. At the same time, if we do get them, I do want to beat them badly because of how much pain they've caused us
As for the rest (Raptors, Washington, Charlotte, Atlanta), I'm not that worried. I think we would beat all four of those teams in a playoffs series. Raptors have two wins against us this season, both of them on a second of a back to back (we've pretty much struggled in every 2nd of a back to back game this season), and one of those games being a horrific, choke loss which won't likely happen again. Granted they were missing Derozan in that second game, but Lowry more than made up for his absence that game. Add to that, Raptors are a very inexperienced team when it comes to the playoffs. Derozan has never played in a playoffs series, while Lowry has only been in the playoffs one year and he sucked. They're a young team who don't have playoffs experience.
Washington, we're 0-2 against them this season. Again, the first loss was a horrific, choke loss in overtime, a game we should have definitely won (also was on the road). Second game, they just outplayed us at Barclays, I won't take credit away from that win. But again, lack of playoffs experience comes in again, and Wall is already inefficient in regular season, I expect him to be even worse in the playoffs. Nene isn't anything great in the postseason either, and that's if he plays (who knows). Randy Wittman isn't a good head coach, so that's another thing against them.
Atlanta, we've played them well in the regular season, and with no Horford for the year, I'm not worried about them. They just don't have enough to trouble us, out of the four teams, this is the easiest series for us IMO.
Charlotte, I think we're 1-1 against them. Again, they're an inexperienced team with some inefficient players as their leading scorers. Big Al will get even more exposed in the playoffs, and while I think Kemba is the type of player to step up his game in the playoffs, I think he'll have trouble scoring efficiently.
IMO, order of difficulty (most difficult to least)
Washington
Toronto
Charlotte
Atlanta
Teams to avoid:
Indiana
Chicago
I'm not adding Miami there, because I would be curious to see how we would play against them in the playoffs, and I do think that it would be a very interesting series. The other thing is that there is no shame in losing to the back to back champions, even if we do lose. A tough 6-7 game series loss against Miami wouldn't be so bad.