The biggest issue with old software is not the software itself, but the the later releases of Operating Systems. Many old programs used DOS and features like VBrun and DLL files. From Windows 8 MS removed many of these old features rendering Games like MidTown Madness, Train Sims etc unusable.
The only way to use the antique stuff in your junk box is to make up an old computer from the dream time and run Win 98 et seq... (If you can find a copy)
Incidently many Government Computers are still running Windows 7 as that was one of the best OS of the bunch and is still very reliable.
New is not always the best ! 
Dave.