Is there anyway to set something up in Airport Extreme to point myawesomewebsite.dev to one of my local webservers? I normally go through and edit /etc/hosts or the hosts file in Windows to point to a local dev site, but I need to be able to reach local URLs using my iPad, which is not jailbroken.

Also, I'm using OpenDNS, so not sure if they may have a way to set this up. (although I couldn't find anything about it on their site)

First bookmark the Apple site Well known TCP and UDP ports used by Apple software products (http://support.apple.com/kb/TS1629?viewlocale=en_US) so you can open ports in the Extreme that is doing NAT, by this blog post (http://theappleblog.com/2009/05/05/how-to-port-forwarding-on-a-airport-extreme-time-capsule/) method.

Then since you are a rank users using an ISP modem service that us using DHCP then your home network public IP can change at a drop of whim from the ISP. Then use a service like Dynamic DNS Free (http://www.dyndns.com/services/dns/dyndns/) So you can always find back to your network When you want to VPN.

Then make sure if you use a software firewall on your Mac that you open ports on that also.

If you want a very quick, secure way (that is very easy) then consider iTeleport (http://www.iteleportmobile.com/home). It might save you you a lot of geek time and command line foolery.