I too started with flight sim so long ago. I first used Sublogic's 767 and then FS4. I recall flying into and out of the default airport, Meigs field in Chicago. I remember the Sears Tower in FS4.

 

My PC back then was the IBM PS (Personal System ) 2 computer. It had 1 megabyte of RAM and 30 megabytes of hard drive space. The IBM salesman advised against getting 60 MB of hard drive space since "there will never come a day that you could fill up a 60 mb hard drive"

I know the feeling.  My first sim was the (comparatively modern) A-10 Tank Killer 2: Silent Thunder:

 

 

 

And here's todays DCS Warthog

 

Makes you wonder what things will look like 15 years from today...