Just a quick post on my second time street-singing on Orchard Road. The experience is largely similar to the first time; hot, humid, sweating and trying my best to fight the surrounding noise. A friend told me about the tunnel linking Wheelock's Place and Shaw...I checked it out and it looks quite promising. Enclosed area (which means good acoustic) and optimal human traffic...I think that's where I'd try next.
A woman actually came up to me half-way through singing "Vincent" and asked me "Son, why are you doing this?", to which I applied, "for the love of music". And then she gave me $2. That felt great :)