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Just to add onto your first point. Most people can barely ride a 250 or a 125 to its (or their own limits). Most people will have chicken strips, improper lean angles etc etc.
Just putting my personal experience on it, the reason I want to upgrade to higher ccs is because I want to do longer road trips (in the 2000+ km range). The longest ride I ever did was 7 hours and my knees were on fire at the end of it because of how high the engine was revving for the whole trip.
At the end of the day, if your first bike isn't going to be a 300, think about what type of riding you're going to do. Long trips? Think about a tourer or sport tourer. Want to go fast or be road pizza (I say that tongue in cheek, no offense to the Ss riders I may get a gsxr which isn't the best idea for a bike that does long trips but it's the most comfortable out of the 3 ss) get a supersport. City riding? Get a low cc bike with some decent mpgs or even better get a drz. Want to make a lot of noise and park at coffee shops, get a harley (I say that tongue in cheek as well).
So long as you know what type of riding you're going to be doing, your decision on your first bike will be exponentially easier.
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