I moved from Windows XP Pro 32 bit to Windows 10 64 bit, starting october last year.
It was definitely not a painless transition. I installed W10 on a new computer, and had to run with both in parallel for three months, while slowly learning to tame that crazy overactive beast W10 is, moving over my software, data, and part of the hardware, and search for replacements for many programs that would not run on W10. Only around Christmas I could finally stop using the old computer.
But it was not possible to transfer everything to W10. In the end I installed a virtual machine with Win XP 32 bit on the W10 system, and I have to use that to do some tasks. For example, everything related to my Garmin GPS requires the old Windows, because neither Garmin nor anyone else ever released 64 bit drivers for the line of older GPS receivers.
And I had to replace many programs by different ones. For example, AutoCAD. Of course modern AutoCAD works on W10,but is way too expensive, and the old version I had will definitely NOT run on W10. So, NanoCAD to the rescue. Same thing with many other programs.
And some features, even hardware, simply went to waste. Instead of my excellent old Soundblaster Audigy with the kX-Project driver, now I'm stuck with a crummy integrated audio "solution" that only offers basic functionality and gets digital interference. Instead of five RS-232 ports now I have just one, and so on.
I gained access to modern software, but lost access to old and very useful software and hardware. So I can very well understand the reluctancy to "upgrade" to W10. The backward compatibility problems are obvious and severe. For me the trigger to move away from Win XP was that all current web browsers no longer supported XP, and that many modern websites don't run in older browsers. I got locked out of many web services that I really need. And moving to Win 7 as an interim step would only have delayed the inevitable. But for somebody who currently is using Win7, the most sensible thing to do is to stay in Win7 as long as circumstances allow.
About virtual machines: It's important to know that one can easily run a 32 bit virtual machine on a 64 bit real machine and OS, and what's far less known, it's also possible to run a 64 bit virtual machine on a 32 bit main operarting system! That's what I was doing to run some modern software, before switching to W10. The limit is given by RAM: 32-bit Windows only handles somewhat more than 3GB, so a virtual machine running in 32 bit Windows can hardly get more than 2GB or so of RAM, and that's very limiting in a 64 bit virtual machine.
I have no trouble using the NanoVNA on W10, through NanoVNA App, but I haven't tried yet updating its firmware from the new system. The last update was done using my old Windows XP computer. I will handle that like I have been handling all other transition problems: When I need to do something, I just try if it works, and if it doesn't, I start looking for solutions, drivers, newer software, tricks, etc..