1. The usual 2-stroke maintenance issues. Not a problem if you are mechanically adept.
2. Hard to answer without having ridden comparable 250 4 strokes.
3. Fuel and oil consumption will be higher (how much depends on how you ride it). It's not really a commuter bike, you'll end up thrashing it around in traffic to try and get the most from it. Where in Aust are you? It might not like hot weather and traffic (my TZR didn't when I was in Sydney).
4. You might, but you'll have fun doing it.
5. Yes. Sportsbikes, especially 2 strokes, are usually in the highest risk category. This is not helped if you are a young and inexperienced rider. Listen to other riders in Australia - insurance brokers as mentioned above are more common in Europe, we tend just to have a few big companies. As always shop around.
6. Yep, but it's not really a good option.
7. Chicks love bikes - just get the right chick! Ones that don't like the cold/rain/messed up hair/clothes might not hang around long......
At the end of the day, these bikes won't be around for too many more years, so enjoy them while you can. But it will involve compromises to your wallet/license/sanity.......