[1] This line actually means 'the higher it goes, the more I can see something'; I just rephrased it.
[2] 'Toriaezu' means something like 'for now'.
- Warning: This is the literature buff in me talking again, so please feel free to ignore. Another metaphorical song -don't they all seem to be?-, this time about challenges in life. By having grown taller, (I believe) the persona means that he has made progress. Yet, he is still so far from the top {sky}. The sun here (I suppose) is the glory of being at the top, which encourages his ambition {heart}. He is aiming too high {too far ahead}, but the higher he aims, the more something (that I think refers to his goal) becomes visible. The way to begin {story of the beginning} his endeavour to achieve his goal, that he has perhaps heard of from others, gives him an idea of what he wants {establishes an image upon my heart}. The wind that blows against him are probably obstacles in his path towards his goal, but he says that the more difficult {stronger} they are, the more attractive he finds the idea of overcoming them {the more it draws me}. The persona thinks life is no fun if one doesn't go against the norm {ways of the world} and take chances and challenges. People forget their dreams when they are weighed down by life's problems, so he advises them to run towards their goals at top speed and without being distracted {going astray} before they do. Original here most likely refers to the path towards his goals that he has devised for himself and the whistling indicates happiness or contentment at the thought of overcoming the obstacles in his path.
[1] "You tsutaerarehen nen Bukiyou ya kara" It was tough deciding whether these two lines stood alone or linked up with the next stanza, but I picked the translation assuming that they stood alone because I suppose that's why the stanzas were separated, right? ^_^
[2] (Merry) This word is not in the lyrics, but it is sung (or spoken, at least).
- The (bracketed) parts in the translation are words that aren't really in the lines, but are implied and which I feel are necessary in the English translation. This will always be my favourite Yuushi song and I'm very happy to be able to provide all of you with the translation. Thank you and Merry Christmas in advance!