The 'file' input type has supported multiple file selection for some time now. The upload function in com_media can be easily modified to accept multiple files without causing any problem for older browsers that don't support the feature. So, is there any reason this not supported in Joomla! yet? I've actually done the modification myself on several Joomla! installations. I'd be happy to submit it the official project if it's wanted.
It's possible to upload multiple files using Flash uploader (Administration > Content > Media Manager > Options, haven't tested) but I'd prefer html5 way.
I don't necessarily have an opinion about keeping or dropping the Flash uploader. I only think it makes sense to use the full capabilities of HTML whenever possible.
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I'd say go for it. It'd be a welcome addition IMO.