Flash,Well, yes and no. I would suggest trying to consolidate old environments into virtual machines under a modern rig. Still, if you want total backward compatibility, you may need one DOS computer (I have a dual-boot DOS/Win 3.1 and Win2000 machine that connects to the LAN with W2K if needed). For running most of DOS/Win 3.1 and older Win 32-bit stuff (e.g. Word 2003 and Acrobat 6), a W2K virtual machine is the thing: very light-weight and nimble, very different from the XP mode klunker. I would venture to say that the W2K virtual machine is all you really need from the Windows realm if you going to ditch Windows altogether and opt for a Mac or a Linux machine. Softwarewise, you may need an office suite that can bridge the gap. My suggestion is Softmaker Office (https://www.softmaker.com/en/softmaker-office), which is very compatible, has Windows, Mac and Linux versions, and is nimbler than MS offerings.
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It is entirely sensible to maintain one or more computers which have no Internet access at all. These can very well be older OS, such as Win7, which can no longer be made Internet safe(r) but can very well function as data repositories, and/or run XyWrite.