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I was hoping for a 250 scooter or cruiser*/ (before I get too old and fat).... but they still seem fairly pricey.
I guess an old Honda Shadow would be the most sensible cruiser. Harleys seem to hold their value.
If I got something I think it would have to be $1,500 absolute max... and I'm supprised how much old 2nd hand bikes go for in the states.
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Too many pot holes and cobbles in NYC for a cruiser I reckon. A bigger scooter or enduro type bike would more comfy for sure. Any idea where you'll be living yet? If you're in the city and just want it to get around Manhattan, a little scooter would be ok. Bicycle probably better though - you don't have to worry about parking and the island is pancake flat anyway.
Less theft, higher traffic speed. You need something freeway capable, specially for trips out to the boros.