It's a fact of live that if there's a computer involved, some day you're going to face the "no longer supported" issue. You can usually live with one thing that's no longer supported, but when you have to update something to accommodate a feature or function that you don't have yet but need, that's where you can run into trouble. When it comes to computer based audio systems, my best advice is to assemble a system that works and don't change it.
Accept that there will be a time when you'll outgrow it, but hopefully you've got your money's worth from the original system and you can afford to assemble a new system to accommodate the upgrade you want. And along with that, accept that there may be some things you're currently using that won't work with the new system, so you'll have to either upgrade those, get something new that gives you what you got from the old thing, forget about that function, or, worst case, keep the old system so you'll be able to use that function when you need it.
My "office" computer is frozen at Windows XP because I use a Lotus 1-2-3 spread sheet that has macros that don't translate to Excel. The computer that works with my Audio Precision System 1 runs Windows 98SE, because the software that it talks to won't run on a newer version of Windows. There's no need to worry about support for anything I'm running on those computers (it's gone away years ago) and hopefully the hardware will last a long time.
I'm with you on all this - my business computer is Win10 because the pro-level software I have to use for what I do can't run on old platforms. But I still run a DOS (yes DOS!) program for bookkeeping purposes because in all truth, the Windows-based bookkeeping programs were all a step backwards in efficiency and speed for bookkeeping including (and I might add, especially,) the ubiquitous Quickbooks.
I run the old DOS program via VMWare which gives me a little virtual XP machine running within my Win10 machine. Those VMWare folks know what they're doing, no question. I used to dual boot with two hard drives - one booting into Win7 and the other booting into XP so I could run the DOS program under XP. But amazingly enough, the VMWare virtual XP machine "inside" WIn10 runs much faster and with no crashes than my old XP booting from a separate hard drive!
So now I don't have to reboot out of Win10 to run a DOS program! And what really blows my mind is that files that the DOS program produces - like printouts and such - can be dragged & dropped from the DOS virtual machine window right over to my Win10 desktop!. It's like reaching into the 6th dimension to grab a sammitch!
But for music - I use so many VSTs (and keep buying new VSTs) that I have to run the latest Windows OS, or not much more than one or two versions back, or I start running into endless problems.
Ah, I remember Lotus 1-2-3. Wasn't that a Corel product? It was a nice spreadsheet in its day. One of the first "3-D" spreadsheets. I used another spreadsheet way back when that was called Lucid 3D, too. Fast, stable, smart. Now it's Excel the spreadsheet overlord, fat and lazy and unkempt - which runs slow, crashes, corrupts the occasional workfile, and hangs with some frequency. The plateau in Microsoft product development seems to have some potholes they don't bother fixing seeing as they have this monopoly....