I haven't watched all of the newest video yet only about 20min of it, but it seems that you do have a good understanding of how to use olimar. It's just that sometimes it doesn't seem like you use the stages to your advantage.
http://www.youtube.com/watch?v=EdndmtBDxJw
In this video the first match you won on battlefield. There were a couple of points where I felt you could have followed up different and gotten more damage, but overall it was a good match. Just watch yourself towards the end. I think you took around 30% because you were trying to rearrange your pikmen for an obvious kill attempt. With the lineup you had at the time and the percentage Chibo was at you could have killed with any of your pikmen save for white.
The second match seemed like it was even then it seemed to just fall apart on your end. I know most olimar mains don't like Frigate, but save for the first part of the stage on the right side I don't really see what the issue is. The transition of the stage where there is a dip in the middle is perfect for olimar. This is where I saw that you didn't really use the stage well. If you're on the top part of that slope you can use F-smash all day long and just rack up damage while they try to get next to you. It usually forces people to jump which is exactly what you want them to do. Even if you're at the bottom of the slope it's good for you because most people can't even hit you without having to get closer to you which you can grab them way before they get in range. Also it gives you a perfect angle for pikmen latch.
Third Match on Luigi's Mansion. God I wish that stage wasn't banned where I am. You were doing all of the right setups as far as throws to upsmash under the ceiling on the edges. Although I did see you use a F-throw a couple times when Chibo really wasn't in killing percentage with it or with the right pikmen, but I assume that was controller error. His last stock he really was only able to come back because you let him break off the pieces of the stage. Never let them break the stage unless you want it. When they try you can Up Air under that ceiling piece and get lots off free damage. Now you may end up breaking the stage yourself doing that, but you at least got 30% or more damage on them for even attempting to do it. Also I see that you liked to whistle armor the gyro a lot on that last stock. I would have suggested trying to air dodge it instead because he racked up a lot of percentage on you just glide tossing the gyro. You still won the match so that was good on your part.
That's all I've watched so far. I may comment more later. Don't think of this as me bashing you because I'm not. I think that you really do have a good olimar. Keep posting up vids.