I recently purchased a game package that consists of Railroad Tycoon II Platinum, Railroad Tycoon 3 and Sid Meier's Railroads! on Steam. Two of these games needed a human (me) to get into the game files to fix them so the games can be run on Windows 10 (or even on Vista or 8).
Railroad Tycoon 3's issue is that it crashes on startup. The fix is to turn on an option called "Disable Hardware T&L" in the Settings dialog. The problem is that you cannot turn this option on in-game if you cannot get the game started.
Epilogue
One cool thing about Steam is that they have a ton of old games from as far back as the early 90's (maybe even earlier). The old games are typically ported, dosboxed or patched to run on modern systems. Although you have to rebuy old games that you wish to play (for rather small prices), it is typically worth the cost to avoid the trouble of working out how to configure a modern PC to run those games.
The problem with Steam is that their updates are often half-hearted efforts. For example, no efforts are taken to maintain aspect ratios of the original games. This makes many of the old games appear uglier than the originals. However, this is typically OK, as you play old games for their game mechanics and functional design more than their outdated graphical design. A bigger issue is demonstrated earlier in this article. Some games are so badly adopted by Steam, you, the user, have to manually configure the game files in order for the game to even run (or at least run without a ton of crashes).
Not all games are fixable. An example of this is Independence War (a game I loved). Both Steam editions (original and sequel) appear to have unfixed game-breaking bugs with no community solutions. These games are only $6, but it's $6 too much for a game that cannot be finished.
