The key difference does seem to be that the jump from $99 to $499 turns DevDays from a conference that you can pay for yourself into one that most people are going to have their employers to pay for.
$499 for a two day conference is pretty cheap but what makes DevDays a hard sell to most managers is that the point of it is that it introduces you to technologies that you're not going be using day to day in your job.
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The key difference does seem to be that the jump from $99 to $499 turns DevDays from a conference that you can pay for yourself into one that most people are going to have their employers to pay for.
$499 for a two day conference is pretty cheap but what makes DevDays a hard sell to most managers is that the point of it is that it introduces you to technologies that you're not going be using day to day in your job.