He can start on an R1 for all it matters, it still won’t make it a good city bike. Unless he’s planning on just having a toy to take out on weekends in the Adirondacks or go to any local tracks he doesn’t need or want a super sport as a commuter/around town bike.
When you’re only peppy from 45mph+ and you can only legally experience the power band pull in 1st gear it doesn’t make much sense.
None of my friends on sport bikes ever want to go anywhere far, not even NYC, they barely put any miles a year on them, they have just as much fun on weekends as I do, they never take them to the track and they all sell them after a year or two. Seen it over and over and over again over the last ~8 years.
You can have more fun on a 300 and be a better rider then many people on supersports. Like I’ve said before some of the most fun I ever had riding is on my 38hp motard and my old ass Ninja 250. Go anywhere, rip through the gears without fear or losing your license, throw them into turns and have very little money invested into them.