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You have no idea of the massive scale of wp.com if you think it runs on 8-ish servers. Otto was talking about wordpress.org, the site where you can download WP software and its plugins/themes & which hosts learning resources & community forums etc. That site gets a lot of traffic & needs multi-server setup to scale as well. wp.com is altogether a different beast.
The uploads folder will need to be shared across all servers running WP so that same static files are available to every instance. Also some 3rd party plugins write to the uploads folder as well. Here you choices on how you want to do it & each has its pros & cons. You can choose to have a network volume used as uploads folder (like EFS on AWS or Cloud Filestore on GCP) or use an object storage like Amazon S3 (multiple plugins like this exist to automatically sync uploads to S3 etc) or use rsync (with lsyncd) to sync files among servers (not a good idea).