I'll be getting an F3 or F4 soon enough.
Been riding a little 250 for a while now.  Fun to throw it around in close quarters with cars in parking lots.

I'm not a gear-nazi.  You wear what you want.

Personally, I would take nothing less than a full face helmet.
I also wear a jacket and gloves.
No boots, no fancy pants.

Hard to find a bike for $500.  Bump it up to $800-$900 and you got yourself a little Ninja 250.  Don't worry about other guys talking about CC's and teasing you.  I ride a little 250 and only over the internet has anyone ever talked trash to me about it.