Bought them all (minus X-PLANE) until FSX.
Didn't necessarily spend a lot, as there was plenty of freeware to keep it interesting. I did my part for awhile by creating real-world airline traffic using pdf timetable data and then sharing that with the community, but once timetable data went all digital, that was the end of that.
I did purchase FS2020, but never found an aircraft that could fly worth a darn...might be my setup(gameport controllers using usb adapters), I don't know. Even bought an HP VR set...that was cool, but made me dizzy.
I'm content with fs2004, it doesn't have all the fancy stuff...but it's smooth with few glitches and lots of great freeware aircraft/scenery.
Must admit...X-Plane does look interesting...might try that out.
There may have been an edition or two of MSFS that I missed. at some point. I feel like there were more freeware addons for FSX than in MSFS2020 but it might be that I spent more time searching for it at that time. My strong preference was purchasing 3rd party planes directly from the developers because I have MSFS 2020 and FSX from Steam and the Microsoft store. When aircraft or other content was purchased from Steam or the Microsoft Store it would only work in that version.
I ended up with versions from both distribution sources because each had sales at different times. With the amount of 3rd party content that I purchased over the years this actually was more cost effective.
I purchased the Aviator Edition of MSFS 2024 from the Microsoft store and I was pleased that this added many airplanes to my MSFS 2020 account. I thought that it would work only in the other direction.
Here are the versions of Microsoft Flight Simulator starting with versions from Bruce Artwick’s Sublogic...
Sublogic flight simulators:
First generation (Apple II, TRS-80)
Second generation (Color Computer 3, Apple II, C64, Atari 8-bit)
Third generation (Amiga, Atari ST, Mac)
Microsoft versions:
Flight Simulator
Flight Simulator 2.0
Flight Simulator 3.0
Flight Simulator 4.0
Flight Simulator 5.0
Flight Simulator 5.1
Flight Simulator for Windows 95
Flight Simulator 98
Flight Simulator 2000
Flight Simulator 2002
Flight Simulator 2004: A Century of Flight
Flight Simulator X
Flight Simulator (2020)
Flight Simulator 2024
I purchased the majority of these along with other flight simulators from other vendors over the last 45 years.
My first experience with a VR headset was negative in the same way. But I found directions about which software and tweaks actually worked, and I have not had difficulties since.