At your age you are right to be sticking with a 250cc-300cc. The insurance on anything bigger will be a real burden to pay. Lots of guys will say you will out grow a 250 in no time, but I say that depends on your expectations and wants in a motorcycle. Any of the modern 300cc's will keep up with highway speeds and are fast enough to get you a hefty fine on any road in the province if you have a heavy right hand. All of them handle very well on public roads and are cheap to run and repair. Lots of folks get caught up in the bigger/better treadmill even though they can't honestly use 50%+ of the bike whether due to a lack of skill or fear of Johnny Law. Either bike is a very solid platform and will hold it's value fairly well. There are always new riders looking for a used 300cc.
Flip a coin, play eenie meenie, write both bikes on a piece of paper and put the pieces in a hat and pick one. Either bike will not disappoint. Just don't get caught up in farkles, performance mods and bling. At the end of the day it's still a 300cc bike, regardless of what you do to it and you won't get back $1 of it on the re-sale.
Enjoy!