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Came across a WordPress plugin called GeoPress today. With it, I could attach cool little maps to my posts. You know – kind of put the Where in Wherewithal (all appropriate puns intended).
Looking around, it appears that WordPress.com doesn’t offer any upgrades that would allow me to pack in non-WP-approved plugins (they do, however, give user a place to suggest plugins they’d like to see made available – I’m on my way as soon as I finish this post). This would include Roy Tanck’s WP-Cumulus mentioned previously. So it looks like my only option here would be to pay for hosting elsewhere.