I just walked into the LBS, said I was going to be commuting and didn't know what I really wanted. He put me into a $300 hybrid that fit me well (he didn't fit me, he just looked at me and said 'you need a 19" frame' and was right.
So I spent probably 5 minutes shopping, and 24,000 miles later I'm still happy with the bike.
A $300 bike will NOT last you 24,000 miles without maintenance. I've replaced the front wheel once and the rear twice (broke an axle once), the crank once and the bottom bracket once, plus several sets of tires and brake pads, not to mention adding fenders, replacing broken fenders twice, adding a rack, many different lights, etc.
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Work: the 8 hours that separates bike rides.