@Brent
Simpler for you...
With uploads I was never playing with that.
With resource targeting to correct URL it is simpler, as they use filters where you can update url on the fly.
Maybe, if you define uploads path in config.php, something could work, but it might need updates in several plugins that should not be super complicated.
define('UPLOADS_PATH', 'some-path/dot.com/with/uploads/');