So how did I go, eh? I'm pleased to report that after 4 months of travelling, I ended up about $500 down (excluding flights).
Overall the money was not as good as I've been accustomed to busking in Australia.
The lack of coins in the US proved somewhat problematic, although I did enjoy not having my bag weighed down with change.
As good as busking around the world is, nothing could top the Olympics for me. I lost my mojo a bit after London, busking less and spending more.
All in all, I give my trip 9/10 for finances, 14/10 for fun.