+1 on all that is being said in this thread about DOS/XP computers and MT2000's and HT1000's. I work for a very large nationwide corporation that has been using Motorola Solutions Inc. radios since the HT-220 (which were only retired two years ago). The company Emergency Operations Centers are still using HT1000's and MT2000's (H01SDD9AA4AN) in UHF, with some interop with amateur radio Auxiliary Communications Service (ACS) elements around the country. Batteries are now becoming an issue, as they need to be intrinsically safe for my employers' purpose, and they are no longer being produced. However, they remain solid on output audio and still put out 4.8 to 5 watts with a charged battery. They also fill the hand and will take hits on cement, and for an organization that has reaped their money's worth, still continue to "save" money over buying something newer and with more options than needed. (Motorola would love to see us buy XPR3500e's to replace these HT/MT series radios.
For programming we have had to maintain ancient Toshiba Satellite and Portege computers running Windows 98SE and XP. Luckily, we have the Motorola RIB and cables. Then there is the age of the radios themselves, knobs falling apart and other plastic pieces that degrade over time.
If we were only supporting these older radios, it would not be so bad, but we are now supporting radios as old as Maxtrac's and as new as APX8000XE portables and APX8500 mobiles. For those that wish to maintain large numbers of HT/MT series radios, head well on what ElroyJetson said above......solid states drives and an old 386/486 is the way to go.
As for purchasing older radios, there are deals out there but be sure you know what you are buying as well.... we have many that have bought 800 Mhz radios on auction sites as well, not knowing that there is no amateur band for 800 Mhz. I also know many that have bought CDM1550LS+ mobiles that only have 16 conventional analog channels, thinking they were getting 160 channels, check model numbers and details.