Check out the Kawasaki Vulcan 500 and some of the Yamaha V-Stars (older ones will be called “Virago” instead of “V-Star”). They make some great beginner/intermediate cruisers, though they’re popular and may be harder to find used.
Three things:
1) A 500cc can haul your ass up a mountain just fine. Weight doesn’t bog down an engine nearly at all. You’d lose a second on your laptimes at Laguna Seca thanks to weight, but your motorcycle won’t even hesitate before conquering hills. Not an issue.
2) As I think somebody told you elsewhere, Ben (site creator) was referring to 600cc supersport bikes when he said “no 600cc beginner bikes.” The concern is power-to-weight ratio, ergonomics, and road manners. With bigger-displacement cruisers, the big problem is bike weight (hard to handle) and not as much the power, though it’s always wiser to bite off less than you can chew.
3) I really hope somewhere in your budget you’re including insurance and gear. That stuff doesn’t run cheap!
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