Hi Jordan, I'd recommend the following.
The Plesk hoster or VPS owner can prepare the environment by himself. See:
http://devblog.plesk.com/2014/09/plesk-and-ruby-on-rails/
http://devblog.plesk.com/2014/10/plesk-and-django/
(full disclosure, I work for Parallels & had our dev team take a look at this question.)