The MS-DOS version of Indy 500 works with stock settings in DOSBox and can use USB Floppy Drives and allow you to use an original copy that contains copy protection. Emulating the Roland MT-32 sound card for PC will give better audio quality.
1. Download DOSBOX (0.74 is the most used and tested version)
2. Setup a folder on your computer as the C drive
3. Copy to or install Indy 500 on the C drive you created
4. Run Indy 500
A steering wheel, though not originally supported, can be emulated via DOSBOX and works fairly well.