Online flying sure is fun, since you get to meet fellow (EHM, and other) pilots.
I always enjoyed our conversations during events and tours, even though the only one using voice was the 10 year anniversary one. The .chat function in IvAp does the job as well. Of course, during the initial and final stages of the flight, there is not much room for typing casual conversation, but pre-light, during cruise, and especially post-flight, I very much enjoyed the personal contact.
Now, why is all this in the past tense? Basically it comes down to one technical issue, and one time issue: Since I am flying X-Plane10 as my primary sim, and X-IvAp crashes my sim, I have not been able to connect recently. The time issue prevents me from doing much more than trying to finish the 007 tour (offline

) in time, let alone dig deeper into the whole connection issue, or get to learn to fly the FSX A318 (I tried, and crashed terribly due to lack of control). My online flying has been so long ago that I just received the dreaded "you are no longer an active IVAO user" mail, last weekend. Mind you: I only have an IVAO account, so maybe adding a Vatsim account may solve my XP10 connection issue ... That would only mean I have two accounts to keep "alive", and that conflicts a little with the time issue again ...
Having said all that, I am sure that I will be flying online soon after finishing the 007 tour. If I cannot fix the X-IvAp issue, then surely with FSX. I have the Pilots of the Carribean Tour assigned, which I fly in the Aerosoft DA-20 Katana4X anyway, so that is FSX bound.
The joy of flying online for me is mostly in the social aspect: I get to interact with other humans, instead of AI traffic and ATC. Also, it "forces" me to better prepare my flight, which I find to be the starting point of the fun of flying. The anticipation of the flight, planning it, and then executing as planned, gives me far greater satisfaction than just jumping in the plane, and taking off to wherever.
ATC is a different thing. In general, online ATC guys (and girls) are friendly and helpful. On the larger airports, you (as a pilot) are expected to more or less know the procedures for that airfield, but on the smaller fields, they usually take the time to guide you through the process, if you indicate you need some help. But I can see how that can be intimidating at first. So why not try to first fly online in, say the Caribbean (excluding TNCM, TNCA, TNCB, TNCC). Good chance you will not even encounter ATC, only some other pilots. And if you do, they will have the time (and attitude) to help you out the best they can.
Setting up IvAp for FS9 or FSX has never been a problem for me. I seem to remember that I just installed IvAp, including the full MTL, and TeamSpeak (which I think was included in the installation process of IvAp, but I am not sure there, anymore). Then I started TS as a standalone application only once to check if the settings were with a Push To Talk (PTT) button, rather than sound-level (squelch) activated, and that's it (I nowadays heve the PTT buttan assigned to a joystick button through Joy2Key). No configuration of servers needed whatsoever, to the best of my knowledge. I am sure I have never read, nor had the need to read, the TS manual. No need to start up TS, IvAp does that for you, and chooses the TS channel that corresponds to the COM frequency set in IvAp (or on the radio stack).
So maybe for Dirk, the solution to the technical side of his problem could be to uninstall IvAp and TS, re-install both with default values, and just take it from there. Try to connect (connection parameters are only entered in IvAp) at a remote airfield in the middle of nowhere (so you won't be in the way of anybody), and just see if you can get connected. If that works, try to connect a a remote airfield in the neighbourhood of a controlled airfield, and see if you can tap in on ATC conversation. Than all that remains is to ask a friend to log on as ATC at some remote airport, connect there yourself, and then try an talk back and forth. If that all works, you are ready for the wonderful world of online flight!