-A ninja 500 is just as good a starter bike as the 250
-No one knows what your insurance will be. Get on the phone and call progressive. You will get a quote in like 10 minutes
-A 250cc bike will haul 2 people. Its not as comfortable as say, a Goldwing, but it is definitely more comfortable than say, a Honda 600RR
-Get the 2008 Ninja 250 if you can. That thing looks totally bad-ass. You won't regret buying it. the older 250's look like they belong on the set of it-came-from-the-80's

Last reccomendation: Don't get a bike if you live in an apartment complex. 80% of the stolen bikes I hear about are stolen from apartment complexes.