If it's for pure city ridding I'd go Super Motard for sure.
On the open road having a faired bike is much more plesant on long rides but in the city the agility and added height of a supermoto would be an advtanage.
I had a DR650 for a while which was a nice bike, not a power house but comfortable enough for shorter rides (all day on the open road not so comfortable), and would be great for your intended use.
Personally I'd lean towards the more offroad/eduro style of bikes with a loud obnixious exauhst so car drivers can't miss you.
Something like a DR650 or a DRZ400 would be a cheaper option to start out with.
I'd be tempted do get a road legal 2 stroke bike, purely for the plumes of blue smoke on start up to offset the telsa/leaf drivers in the city.
A guy at work had a KTM Duke 200, reckoned he was getting between 2-3 L/100km.
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