Hi Flanker, joining a squad is a good idea, but not necessarily the best first step for getting online. To go online, read the end of the first post here:
http://forums.ubi.com/showthread.php...Off-The-Ground, about downloading and connecting to Hyperlobby. Hyperlobby is a free tool that lists and lets you join most IL2 online servers. There is also X-Fire, between the two you should have access to nearly 100% of all public servers.
You will need to update to the latest patch of the game, 4.11+Hotfix. Some of the servers still run on the last patch, 4.101. Search for patching information in another help thread, and use this for switching between the two:
http://www.thefoxbats.ch/forums/view...php?f=10&t=278
Once you're online, you can get your buddy to join you on whatever servers are available, instead of figuring out how to set up a server yourself. You can join an empty server if you want to fly just with your friend. I recommend my squad's (334th) server for that, as a lot of its maps have computer-controlled (AI) planes you can shoot at. Or you can join one of the more popular servers and fly with other players. Be ready to get shot down often though, online players are much better than AI.
Have fun!