Remote Server Maintenance through HS network
 

I'm putting a new system in my wife's classroom that I would like to be able to maintain remotely. I won't be able to ssh into the system becuase it is on a highschool network that I have no control over. I have a VPN running at home so I could setup the system to connect to that, but I'm not sure how reliable that is plus I will then probably have to setup two NICs so that the system can also be present on the school network. Seems to add complexity and possible problems.
Are there other options here? I will do the research, I just need a starting place.

Windows remote desktop has been implemented in linux. There is also vnc.
vnc at least is configurable as to what port to use.
I would start by scanning the school with nmap to find any openings in their firewall

Why don't you ask the school's sysadm to open a port for you and forward it to the LAN IP:22 of your wife's system. Then you can ssh in and do as you please (even run vnc over ssh if you'd like a GUI). Restricting ssh logins to your wife's system to ONLY key-based authentication (simple logins are not allowed) would be a good security move.

Sorry, I guess I wasn't clear. I'm not looking for a software solution, I'm looking for a network one. I admin several systems currently so the issue isn't using ssh or VNC it is how to use these technologies without having any control over the address of the target machine or any control over the firewall it sites behind.
This is exactly what I can't do. Questions like that will invariably lead down the road to 'sorry you aren't allowed to run anything but school computers on the school network'
What I'm looking for is a way for the system to dial out back to my network on its own. I think I see two options:
1) VPN
2) SSH port forwarding

Both of these will fail however if there are network issues so I would have to script them to re-configure themselves at some interval.
Is there an options 3?

Well, maybe you need to re-read the LQ Rules: http://www.linuxquestions.org/linux/rules.html

We will not help you subvert the school's sysadm's security policy.

This is something you will have to negociate for yourself.

Go ahead and ask, nicely, with reasons why you need this access, and why you believe it to be secure, and maybe they'll agree.

If they don't agree, then that is their right: They own the network.

Otherwise we can not help you.

You obviously don't work in education. No one owns the network. It was put in 10 years ago by a contractor and it is running on hope and prayers. The 'network admin' is a gym teacher who once took a Power Point class. There are no 'acceptable use policies'. I'm simply in a 'better to ask for forgiveness than permission situation'. If you don't have an answer for me that is fine. If it makes you feel better for me to make up a different story I can do that too. I'm just trying to solve a practical problem and I was hoping someone with some experience would have a solution.

Think about it abstractly for a moment. There are ways to accomplish what you want, but as tredegar mentions, subverting the rules of the network you're on isn't a good policy, and we cannot help you accomplish that. This question gets asked and answered fairly often. Googling will probably point you in the right direction, and you don't need to do any fancy searches either. The only technical term you need in the query is ssh, everything else is common English (or whatever your preferred internet browsing language is). Its not that we think you're in the wrong by trying to get past a seemingly stupid rule, but we can't (directly) aid you in accomplishing it. What you're doing here is having somebody pay for dinner under the condition that you don't order lobster, and you're asking us how to still get them to pay, but also get lobster!

Best of luck in your search, I don't think it will give you too much trouble.

Peace,
JimBass