I hosted my own wordpress blog for several years on various virtual private servers, and was hacked multiple times. Just got to be way too much work to admin the site. I use wordpress.com currently. It's less than ideal, but I think you're underestimating the amount of work required to secure a site long term, rather than simply install one. For most lay users, insuring that their host is keeping python up to date, that the security permissions are correct on each file, and that every plugin installed is 'safe' is more time consuming than it's worth. I'm not up to speed on the state of static site generators, but that's got to be a better way to go for most users.
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