Keeping the hardware and upgrading to the new OS (Windows 10, even if it's "free") is not worth it, is what I concluded more than a decade ago. I have saved tremendous amount of money and headache by buying separate hardware for the new OS, and keeping the older machines with the older OS intact. I know many people who were forced to buy a printer after upgrading to Windows 10, and I got such an "obsolete" printer for free from a friend, because I stuck with Windows 7. Think of drivers, too, like for printers. It's not just the applications that have compatibility issues. If I wanted a newer OS, I bought a separate machine (discounted or off the clearance section) with the new OS already installed. I've stopped "upgrading" OS on one machine after Windows 98. Somewhat off topic, but people need to reconsider their PC/MAC upgrade strategies from now on. This is to add to the helpful comments by MX3MZ1. Luckily, a newer version was available (open source) where the maintainer added the "compatibility mode" feature that allowed it to work on different versions, from Vista and beyond. I had another software designed for Windows 98, which worked on XP, but did not work on Windows 7. I think you will be pleased that you did. I highly recommend that you make the move to OR.
Plus OR is completely free for download and all updates, which are regular and have added many additional features. Everything for MSTS runs just fine under OR, often better, and with better graphics.
Its technology is far more current, and it has a regular, stable development cycle, unlike MSTS which is way out of date technically and is basically dead software. I now use Open Rails to run all MSTS content, and I recommend the same to you. I will have to check when I get home later! I honestly don't even recall if it runs ok on Win 10 with current updates, it's been so seldom if at all lately.
That said, I have not run MSTS itself in a long time, probably also including on Win 10. I have and run several railroad simulator software packages, and I have a ton of content (locos, cars, routes etc) for all of them, but particularly MSTS.
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