Well from what I can see, you don't have much experience with cinematography. The overall feel is there, its just things like a shaky camera and a long mono-tone speech take away from it. Here are some points I can pull off the top of my head, I'm no professional but I like to think I know what I'm doing; to a certain extent anyway. Here goes:
- Get a tripod. Don't film everything on it, but it'll help with the camera shake.
- Get creative with your shots, zoom, focus etc.
- Try playing with your footage (ie editing colour, contrast etc.) in a post-production software like Premiere or Final Cut. Even iMovie has colour editing now. But please PLEASE don't use any cliche effects. If it's a pre-made effect, don't use it. 10,000 other people will already have used it and its not original or creative, which is what you're going for in the film industry, or any type of art for that matter.
- The last scene with you talking was VERY boring. You can barely hear what you're saying, and worst of all you're filming UP towards a bland sky. Not only does that make everything else darker, its a pretty boring backdrop. It's not a solid rule (there are no rules in any form of art and if there is, break it) but try not to film up towards the sky, especially for scenes like that.
- Try to get creative with your "Why?" section. Instead of just filming you telling people about it, SHOW people why. Film (or even better record audio with a microphone) yourself talking, then film a bunch of clips that represent what you're talking about and put them over the audio recording. It makes it much more interesting, and it'll convey the message better without boring the audience.
- Memorize your speech before you do it in front of your camera. DON'T fidget, shuffle, etc. and LOOK AT THE CAMERA; YOU'RE TALKING TO SOMEONE HERE. If you screw up, do it again and again until you get it perfect. Remember, you only have one chance to impress, its not likely that the person evaluating your video will watch it or look back on it a second time.
- Careful on your song choice, the first one was really good, it set the atmosphere quite nicely but I'm not sure that the second one will be as appreciated as much by an older audience, if you know what I mean. Try to choose songs that doesn't cater to one specific group, or songs that won't bother certain people ie. try to avoid "explicit" songs.
- On that note, just make sure your video appeals to everyone, not just skiers, skateboarders and young people. Ask older people to watch it and give you their honest opinions.
Holy balls thats long, and I'm sorry you have to read through it but it'll help, really. If anything just remember, you're not making an edit for your friends and family to enjoy, what you send in will be watched and critiqued by a much older and different crowd, so keep that in mind. Try to tell a story with it, really showcase the best of what you can do, its your chance to shine. Go get 'em tiger.