I'd like to toss in a recommendation for the Triumph Modern Classics line (
Classics | Triumph Motorcycles). The Bonneville and Thruxton are considered excellent starter bikes with tremendous reliability. The Bonneville is comparable to the previously-mentioned HD Sportster (in fact HD originally introduced the Sportster to compete with the old Bonneville, which was dominating the segment in the states at the time of the Sportster's introduction).
The Bonneville & Thruxton (basically a factory cafe racer version of the Bonnie) are good as starters because they are easy to ride but aren't as limiting as some others. They handle simply (though still fun/rewarding to ride hard), and while at 865cc and 67bhp they are easily powerful enough for highway riding they aren't so powerful (read many/most sport bikes) that you feel stifled and frustrated in stoplight-to-stoplight city riding (should be a consideration if you plan to ride mostly in town). They both offer very comfortable riding positions (should be among your top considerations; get a bike that physically fits your desired riding style).
If buying new, I would recommend against buying something in the 250 range, as you will quickly get confidence on a good motorcycle and just as quickly become frustrated by the lack of performance in a drastically-undersized bike. No need to switch bikes in a few months.
Back to Triumph: I also really appreciate the lack of pretense associated with riding one. There are good bikers of all types, but for some of the mainstream lines it becomes more of a poseur costume party than about the riding itself. Not much of that with this line. It's just a fun bike to ride, and turns plenty of heads, though it is also bonafide grandpa bait. Lots of old fellas stopping you to ask you what year it is and tell you about the one they supposedly owned back in '68.
Triumph also has a bunch of great modern rides in the sport/street, cruiser, touring and dual-sport areas, if any of those float your boat. Go read some reviews on-line. They are a darling of motorcycle magazines. Unfortunately you'll presently have to go out of state to get a new one, but it's easy (I did), and good local service is available.
Don't buy something just because "that's what everyone else rides". Motorcycles at their very essence are about individualism. Get the bike that is right for you, take your time to figure out what that is, and listen to your inner voice, not just recommendations from others (me included). And for goodness' sake, take an MSF class (the one at OSU-OKC is excellent) and get your endorsement BEFORE you buy, and never act like the squid hooligans in that video.
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