I bought a CBR300RASE as my first bike. 220ish lbs, 6'0, 0 road bike experience, plenty of dirt experience. I bought it strictly for insurance savings vs a bigger bike, and the fact that I want to be able to use the entire bike. I don't plan on going a billion miles an hour and a 300 is more than enough to handle the road speeds in canada. In my town you would be lucky to get out of second gear on a 600cc+ bike, and my commute for work is only about 20km each way.
Depreciation on a new small bike is laughable. I paid $5066 and I might sell it for 3500-4000 in a year or 2 in good condition. $1500 depreciation? Meh. As of right now if I tried to sell my 2013 car I bought new, I would take a 10,000$ bath. That's a lot harder to stomach.
About the highway, it IS only a 300. Don't expect to be doing wheelies at 100mph, or even holding 100mph comfortably TBH.