1 site @ $100/day or 100 sites at $1/day? Whats your approach?

I agree... I like to feel safe online.
The internet in virtual. I see it as virtual property.
Just like your computer crashing. It could all be gone, that is always in the back of my mind.
Never put all your eggs in one basket
1 main and 4 small or 9 small sites, using different networks etc..

 

Think quality over quantity.. But that's not to say you shouldn't have more than 1 site.
10-20 sites are very manageable...

 

Yes quality that you can control, not quantity that has to be outsourced and thus slowly lose control.