Hi guys.
I want to rep Pit the best I can where I can, so let me try a crack at this matchup for a sec. Soon, I'll be able to produce results because next tournament I'm going half and half like I keep saying I'm going to. (Pit and Wario)
For Olimar:
STAGES:
Conservatives Stagelists or Extreme, Olimar will no matter what ban RC (unless named L_Cancel) unless they have a pocket character lik MK themself. There's no point in not banning RC. If they don't ban it, think about your character and think about what they are thinking; they might be trying to mindgame you to switch or NOT pick RC. Do not do the latter, but do the former if you feel that Pit won't be able to handle some gay counter character that's better than Pit on RC.
More conservative stagelist?
Reccomendations:
RC>Smashville>Frigate>Lylat>=Castle Siege>Delfino>Brinstar?
More liberal stagelist?
Norfair>RC>the rest
Explanations:
RC doesn't need explanation. But I'll abstract it.
Give no quarter fighting Olimar up close. When you start, you must keep on him on this stage to advantage of his weak recovery, just like any stage, except, this stage will help you in the movements. Try to focus attack when the stage forces him to move, so he's not just standing his ground, he's got to move.
You have free reign for recovery here. Just don't use WoI stupidly. Recover low to avoid being gimped by a purple if you do use WoI, glide safely, don't use glide for offensive purposes unless you want to be random-upsmashed because it's hard to see Oli here a bit since he's a bit small.
I won't give much else, since it's not going to be common you get to fight Oli here.
Smashville:
Camp top platform when you can for camping purposes (when it's on the sides), but when it's in the middle of the stage try to lure him onto it or in the air in general so that you can take advantage of his weakness as was discussed earlier, his under side.
To lure him, simply get a good grab on him if you can anticipate one of his grabs. It's hard, because you can't spot dodge, you'll get grabbed. you can roll, you'll get smashed. You have short hop past him while air dodging, and choose where to land, either in front or behind, and how far away to land. If you can time it right and he predicts your attempt to grab him, he'll likely either grab (if you're in front of him) or smash (behind). Try powershield the smash if he's facing away, and then grab.
After the grab, throw him up or down (both make him go up, but use up throw when he's at low percents), and then follow up, while trying to keep him on the floating platform. I believe it will be very difficult for him to manuever around your uairs, mind-games to bair or anything. He either needs to jump up and stay high away from you, which puts him in a worse position... Or he will shield. Let his shield lower.
Use short hop uairs when he's above you, full hop uairs when you see a whistle because he's so high up. Landing a successful uair will lead to a weird trajectory of which Oli will be sent giving you the upper hand in the scenario (for edgeguarding purposes or general setups)
This is generally my take on the matchup, given that you choose a stage more regular like SV, or a wonky or different stage like RC. Don't pick polar stages like FD or low-ceiling stages like Halberd. The only reason I suggest Brinstar is because it helps you kill faster on the sides and you can plank, plus lava really hurts Oli more than it hurts you.
Tell me what you guys think. (sorry for this being so late)