There is nothing wrong with either one. IMO, if you are just getting into the game, buy something used and cut your teeth on that first. If you just gotta have something new and shiny, then pick that one that has the right color scheme or has a local dealer that seems to make a positive impression and go with it.
Everyone has their own preferences. If was just coming into the game, at this stage in life, I'd likely look at a Honda 500 of sorts. Not sure if there is much difference in cost of insurance from a 500 to a 300 or 250?
To me, it would provide a little more rounded performance for around town, out on the country roads and 400 series highways.
Then again, if I could pick up a little cbr125 to bomb around on, I'd be in heaven too. But, I'd pull the trigger on something a couple of year old with no visible scars or abuse and try and pick it up for cheap.