You can't upload video to your WordPress.com blog at all without purchasing a VideoPress upgrade for roughly $60 per year.
VideoPress is an impressive service that seems designed and priced for moderately large-scale operators. If you want to experiment, or host just a few videos, you're much better off hosting them on YouTube or your own server, then linking to the video from within your WordPress blog, as described in this chapter.
WordPress.org contrast: As with audio, you negotiate disk space costs with your hosting provider, as well as support for streaming video.
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