[Learning Python]

+1 for Learn Python The Hard Way

[VPN Providers - suggestions]

I work with MANY VPN companies on a daily basis so hopefully I can help. Sadly most of the companies we work with have some sort or US presence but here are some I would recommend in no order...

StrongVPN

PureVPN

Private Internet Access

My Expat Network

SurfBouncer

Astrill ((start here)

[Air Gap flaw]

"At best, an air gap is a high-latency connection" -Ed Skoudis - DerbyCon 3.0

[VPN Initial connection insecurity]

Brendan O'Connor created a solution in ruby that you might want to check out. You can provide your creds in a file and it will connect for you. add the ruby script into a script to start you ssh session and it should authenticate you and connect.

https://github.com/ussjoin/portalsmash

[Build your own hacking/security/pen-testing lab!]

Just my 2 cents....

For my personal testing lab I use a Proxmox server that I set up on a older desktop. By using the turn-key-linux packages available through Proxmox, such as OpenLDAP, Radius, Tomcat, file servers and more, I am to simulate a lot of network setup I have encountered. Granted I have pumped some money into my set up, it works so well for me.