Windows 8 was a complete waste of time (think of it like Vista). 8.1 was a marked improvement. Windows 10 is much better again and can be thought of as the bringing together of Windows 7 and 8.1 in terms of user interface. As Justin says there are things you should do on Win10 to tweak it from a privacy and functionality perspective.
In relation to older software and O/S's I find it easiest to virtualise the physical machine so that it can be moved on to any new hardware I run. That way there is less risk of an old machine going "puff" and me loosing any hope of recovery due to the age of hardware etc. Another good thing about VM's is you don't have to have a whole lot of physical systems kicking around taking up space. They all reside on a singe machine be it Mac or Window or Linux, just run up the VM you need and away you go.
If you are needing older style ports like RS232 etc then there are conversion interfaces that will provide that on new hardware.
Anyway, there are plenty of options that allow you to continue to use your old stuff while not having to be held back by their limitations.
Cheers,
Sean
“Only two things are infinite, the universe and human stupidity, and I'm not sure about the former.” - Albert Einstein
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