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I know that this is not a very secure way to operate a server, but it is for a personal server that is on a private network. I would prefer that it auto logs in so I don't have to attach a keyboard for this sole purpose after the system reboots, and can just go straight to ssh-ing into the machine (no clue if that is a correct term).

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possible duplicate of Disable password prompt upon startup in Ubuntu Server – Mark Kirby Aug 4 '15 at 6:53
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If you're going to ssh into the server, you don't need to have anyone logged into the computer, you just need to install an ssh server.

I don't understand why you need an auto login, but if that's really what you need, this is an excellent guide.

http://littlesvr.ca/linux-stuff/articles/autologinconsole/autologinconsole.php

All it requires is for you to modify a few configuration files.

If it what you want is to not enter a password everytime you ssh into the server, then this explains how to do so:

http://www.linuxproblem.org/art_9.html

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Based on what you said, I wouldn't have to log into the system with any user to start a service defined in the crontab? I want a file server system to start, and I have it set in the crontab for my user, but, if I'm understanding this properly, I wouldn't have to have them be auto logged in for the service to start? – superuser1995 Aug 4 '15 at 3:30

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