to the point; talking about simulators; I used to play Airport Inc. an airport simulator which was made before 200 I think, really old but most of the time satisfying for me. I also played the airline sim games mentioned before; pure rubbish
Airport Mogul in the US. I spent many a Saturday morning on that game. Entirely linear, horribly animated, but I was just so happy to get a 777 to fly to my airport that I didn't care. The two versions following that game were terrible, but the first one is still playable, even today.
I had a PC simulator called Airline by Efzed. The first version I had was sometimes unstable, but still fun. It wasn't anything to become addicted to, but when you had a couple hours it was alright to boot up and build a legacy. The next version was so buggy that I couldn't start an airline, and I was amazed they even sold it without doing any testing whatsoever.