I have a vast experience with flight simulators, and many, many flight hours.
I began with FS2002, then FS2004 before quitting flight simming, due to lack of time to devote to it.
My favourite airplane of all time is the Level-D 767, which I believe can not be surpassed in terms of sheer realism unless you actually step into an actual 767 cockpit or buy a professional flight simulator. The PMDG 737 airplanes were pretty good too, especially with the FS2Crew mod. I also used to have most of the greatest and most popular freeware aircraft, some of which being truly payware quality, such as the Project Fokker ones. In addition, I had some payware scenery and some freeware, but definitely not as much as aircraft.
I knew how to fly ILS and successfully take off and land most airplanes under a good deal of conditions, save for Airbuses, which I could never learn to fly. Oddly enough, I couldn't fly VFR.
I flew for a couple of online airlines, like JAL and Cathay Pacific, but that was always shortlived because I couldn't be bothered to fly on demand.
Regardless of all that, I still found VATSIM intimidating, and could never do a single flight on it. I was always afraid of being a hassle to the controllers, and the so called "help guides" were invariably several pages long and had gazillions of rules that everyone had to memorise in order to avoid conflict. If anyone thinks racing on a server is intimidating, they surely DON'T know about flying online.