DOS,WinXP and Windows7 work well.
Here is the following that I have used for over 20 years now:
This is just the commercial equipment.
DOS 3.1 on an older Toshiba Satellite with a floppy drive:
Motorola: HT1250, Saber, Astro Saber, Maxtrac, Spectra,and Spectra Consolletes
Yaesu FTH-2070/Vertex Duo
Icom IC-400U mobiles
Windows XP Pro with a serial port and USB programming cables: (Dell D810,Panasonic CF-53/72/29/30 GoBook VR2)
Motorola XTS and XTL radios, CDM series,HT1250,Visar, Astro Saber III, DTR series and MotoTrbo
Icom IC-F1020/2020 mobiles, IC-F43GS,PCR-1000
Yaesu VX series handheld radios.
Windows 7 on a GoBook VR2 has programmed all of the previous mentioned radios with serial and USB cables, some in a virtual environment though.
Pretty much any computer made the time the radio was made will be able to work. But it is usually easier for the Pre Windows 7 computer to have a serial port. And slower is better for the older radios. Sometimes the virtual environment doesn't work so well. And some USB to serial adapter do not work. I have had good luck with Keyspan adapters.