Hi! I'm Eric, a computer expert who's been paired with you through JustAnswer.com. I'm reviewing your question now, and will return w/ an answer soon!
Hi Peter! I'm terribly afraid that your older version of Flight Simulator will not work with Windows 10. The primary reason for this is that the game was written to be run on older 16-bit operating systems (Windows 95/98) -- these are compatible with newer 32-bit operating system, but not supported on 64-bit operating systems like Windows 10.
I'm sorry I don't have better news to pass along. :-(
I'm sorry the answer wasn't what you were hoping to hear. I am glad to ask our customer service team to refund your charges, however.
There are some emulators available to run older apps, and possibly there is one to help. There are no guarantees, and to backup Eric on this, we can only give the answers to the best of what is available for solutions. Sometimes those answers are not what a customer wants, however it is an answer that solves the questions. Maybe not the way a customer wants, but still the answer to the question that was asked.
With said, and with your question, there is possibly a solution, but like I said, no guarantees it will work. There are some older app emulators that can fool the apps and windows 10 to allow them to work. This is one such software that might help.
Understand I have not tried it, but it might be a solution. If wanted I can try to supply other application links to try as well, but please understand Eric gave the correct and best answer available. I tried to PM eric to give him this information, but could not find his info to do so using his name. So if Eric is still working with you he can take this back if he wants to proceed.
Thanks in advance.
UPDATE: I also found this page for you to go through as it might be an even better resolution as it seems to supply a walk through for you.
Was this of any help for you both?