I am in the fortunate position of having a couple of buddies who also play DW, SH4 and SH3, and so I usually just get them on teamspeak or the telephone and arrange it that way. I tend to get my ass handed to me on DW!
I've noticed that SH3 and SH4 tend to be more stable online via Hamachi as a virtual LAN game than as a straight-up multiplayer via the net, which is true of a lot of games and sims (in fact it's the only way I can get Falcon to work online). In case you've not come across Hamachi: It is (in its most basic form) a freebie download utility which enables you to create a multiplayer game with your buddies on a 'virtual LAN network'.
I've also noticed that there are multiplayer match up options on the subsim site and I daresay things like gamespy, hyperlobby and the like offer the possibility of linking up via the chat.
You might also want to consider looking at some of the wolfpack league stuff and virtual flotillas that there are if you are looking for something a bit more reliable. I'm sure there are many virtual flotillas which would welcome a keen new player. Or if you are feeling ambitious, you could start one yourself and advertise its presence on these forums.
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