Hello,
I am going to be running a webserver and would like to know which is better to use for logging into the server to do work on it, telnet or ssh. I know SSH is good if I am the only one using it, however, I have a friend that is not within my network who will be using it as well. Should I set up a VPN usable with SSH or should I use telnet based logins?

If the port you use for ssh is forwarded to your machine in the LAN, there is no reason that user can't also use ssh. Put both your user names in an "AllowUsers" line in /etc/ssh/sshd_config to block attempts against system users. Alternately, you could add yourself and the other user to a group created to control ssh access. Then use "AllowGroups" instead. Also make sure that you disable root ssh logins. Often, a different port is used for ssh to reduce the number of script kiddie attacks. You could translate the port number on your router/gateway so that the port is translated to port 22, or you can change the port that sshd listens to.

sorry for the late reply work and midterms.
In any case, the user is not within my lan, nor is the port I am using being fowarded (I dont think the default ubuntu kernel has port fowarding enabled, although I can always compile a new kernel if necessary). However, if i enable port fowarding wouldnt that require me to create a tunnel on the server machine (as well as the clients) in order for other users not within my LAN to use it?