How do you guys try to get in?
How do you guys go about gimping?
Share some knowledge with me!
I like these questions! :D
Approaching Olimar is possibly Kirby's most difficult challenge in the match-up. As we know Kirby's aerial approaches can be punished from a defensive opponent and Olimar's usual choice of action is to go into defense mode when someone gets close. He's either going to Shield or become evasive, both of which make it difficult for Kirby to do what he does best and go toe-to-toe with the opponent (or in the case of B-air, 'toe-to-face'). If Kirby tries to approach when on the ground he has to watch out for Pivot Grabs as well, which, unfortunately due to it's ridiculous range, generally beats out Kirby's grab game.
All of the above is also complicated by the fact that as Kirby squares off with Olimar he's getting Pikmin tossed in his direction at every opportunity. For the most part I would say you should just ignore the Pikmin Toss with the exception of incoming Purple and White Pikmin. You'll want to avoid getting hit by the Purple since they will knock you around and you'll want to make sure to get White off of you since they deal extra damage. Other color Pikmin will only be doing small amounts of damage so it's best to keep your focus 100% on Olimar unless you're still at a far range.
When you get up close to Olimar you should already know what Olimar is going to do next, otherwise you're just going to be throwing out random choices and crossing your finger (and this is not the kind of match-up where you can't afford to do that). 'Reading' Olimar is actually more of accepting the fact that he has strong options against you but then not putting yourself into the position where the options will work.
For instance, if you want to get a Grab on Olimar don't do the usual 'run in and hold shield' tactic - he's probably just going to Pivot Grab you. Instead, 'read' the Pivot Grab and accept the fact that it will beat your 'run in and Shield' tactic. Set up the situation in which Olimar is going to Pivot Grab; you can now avoid it.
One thing to keep in mind is that the 'reward' for successful reads is going to look small for the Kirby player. In fact, the advantages could even seem non-existent. Just remember that in this match-up it's the little things that are important, not because they add up over time but because they help get you to where you're going: taking stocks. Taking stocks from Olimar is usually a very sudden turn of events. He's either going to grab that ledge or get gimped; he's either going to whistle through your F-smash or get KO'd; etc. It's the level of play you build along the way that gets you to that point.
So if you find yourself making 'good reads' but feel like you're still struggling to get anywhere, just keep it going until the big opportunity presents itself. The important part is to make yourself a threat to Olimar and to be able to roll with the punches.