If your data is stored on a server that someone else controls, you can't reliably destroy that data. Even if it appears to have been destroyed immediately, there could be other copies somewhere. So wherever possible, sensitive data should not be stored on someone else's server. Even in encrypted form.
encfs is really easy to setup and use, everybody should be using it, especially on VPS's:
$ sudo apt-get install encfs
or: $ sudo yum -y install fuse-encfs
then: $ sudo encfs ~/.encrypted /home/private
the /home/private folder is where you place your files (web sites, etc.). ~/.encrypted is where the encrypted version is stored. when prompted hit 'p' for the default paranoid mode, enter a password and you're done. read more about it on the homepage[0]When you are done with a server and need to secure delete, use shred -- which is installed on both RHEL and Debian based distributions:
$ sudo shred -fz ~/.encrypted
$ sudo shred -fz /home/private
[0] http://www.arg0.net/encfsProbably better to use ecryptfs or dm-crypt.
Two examples: (Depending on the settings you choose) hard links might not work at all, and renaming can be very very slow. Both of these are common in certain applications.