From one song, this song, could you create a mental image of the singer? What do you see?

[Pikopoku]

Hearing this song for the first time can you depict an image of the singer? Do you think he is a professional or amateur? How long do you think he is been singing and playing guitar? How is his guitar playing? How old do you think he is?

I sometimes do this for random artists I’ve never seen and then look them up and see the differences. 

Anyhow, what do you think about this cover? How can you tell?