What do you do that involves those legacy OSes?
Support industrial systems either directly keeping it running which here is installing the relevant OS on a new hard drive then drivers and system software or indirect support needing legacy software. Of course these systems should have been upgraded but a combination of nobody made responsible and/or no funding from the bean counters.
XP > Vista was a breakpoint at which software for NT4, Win95-98 & 2K mostly would run on XP but nothing later.
Just last week I put both XP and Win7 32-bit on a laptop then various versions of a software package so it can be taken to a customer site with the aim to interogate an existing system we did not supply with a view to us supplying a modern replacement.
.... Get a Chromebook would be my advice.
If you don't already have a Google account you do need to create one when you first set it up, but it walks you through the super simple process and you're up and running in minutes.
When it's set up, there is nothing more to do other than just use it. It will make your CS envelopes system seem over-engineered!
A quick look at what a Chromebook is has left me little the wiser, however it does say that it is basically useless offline and that it needs Google Cloud printing, whatever that is. However, I have always used the library as I have never had a printer. (*) I think that the possible problems are so great that I will go to my low-tech envelope method.
* - Actually, I do have a printer, which came from my father, but it is so old that it probably has ‘Crimean War Surplus’ engraved on it.
There is a market, perhaps too limited, for something like a Chromebook but independant of being tied in to Google, Microsoft, Apple, Amazon etc. Having
- web browswer e.g. Firefox
- email e.g. Thunderbird
- PDF reader e.g. Foxit
- Office application to read and create *.docx, *.xlsx, *.pptx and generate PDF e.g. Libre Office
- organiser / diary / contacts
- photo viewer
- audio & video player e.g. VLC
- simple photo / graphics editor to put images and screen grabs into email & documents
- physical USB ports to save & backup
- connection to a TV ideally HDMI as well as wireless.
would meet 99% of requirements.
Essentially this is what I have used Linux based since 2016/7.
Getting it running though is a leaning curve. I don't claim to undertand the installation and configuration that can not be done in a GUI (Windows style) way but has to be done through the terminal ( in MS terms DOS command line ) just blindly copy and paste plus keep notes for the future.