just bait it Tesh; its really not that hard to do. I just attack when he makes the sound, because by then the armor is usually off. multiple hitting moves like fair or utilt which i usually do after uair chasing the opponent in the air, seem to have an effect. I did that on Rich when we played and it owned him for the most part. Especially if the oli loves to whistle like rich, i just bait it and own him for it. like throwing out uairs to a dsmash when he lands.
Attack oli at a 45 degree angle ( its his blind spot) and chill at outside of his grab range then punish him if he throws out something due to your closeness or utilize quick approaches head on. It is definitely punishable by a kill move, u just need to know ur frame data so u know when u can throw out an attack to hit the lag. Land camping Olimar is really simple from my opinion, its getting the initiator thats hard at times. Just use the blind spot and baits to force a reaction, stay where he cant really throw anything without it getting punished by a run in grab dash attack or spin dash. Its pretty effective for me.
EDIT: LOL I just watched the first video. Ill help you with the situations you were in; Oli has a good grab with range. Iono why u dont up b out of situations when you are continually getting followed up. springing out of situations you dont understand is among one of the greatest tactics in this game. Its a get outta jail free card that few characters have with such benefits.
And dash attack is a great initiator; except when you think you have oli's grab range and grab 5ft away from oli after sitting in shield for a decade not doing a thing. I know u are a better player than this man ( at least I hope). Just look at your matches; seriously just watch ur own vid. Theres such absurd decision making by you. Rich didnt even do anything ****; u beat urself.