Let me also add that if you're running Metaframe XP, you have the capability of scheduling a reboot, if that's what you really want to do.
As for services starting up w/o being logged in, that is generally true, but it depends on the service itself. Some of them needs some intervention to get them going, some don't. I never trust anything, so I always go back in after a reboot and make sure things are ok. Especially after installing updates, I've had instances where stuff didn't work anymore.
As for being nervous about losing the connection during a reboot from home, you might want to consider something that allows you to have control of the console remotely, regardless of the state of the operating system. Like HP/Compaq Proliant servers either have built in capability or something you can buy that will allow you to do this from over a network or modem connection. I'm sure other manufacturers have similar stuff, I'm just not familiar with them.