We have dozens of PC's in need of OS upgrades from 64 bit Vista. Why? Because that was our last upgrade cycle and migrating hardware with Windowns is, well, you avoid it for as long as you can.
Windows has always made this a painful experience. Our machines take several weeks to build. You have to install, configure and license dozens of applications and take a couple of weeks to make sure all is well before replacing old machines.
Why is this the case?
Because the underlying design of Windows OS does not create a separation between OS and apps.
If "C:\Program Files" could actually be an independent entity (the "P:" drive?), upgrading hardware and OS would be child's play. Buy new pre-built computers, move the P drive over and you are up and running. Your employees could even have machines at home and be given a drive with all the apps installed to work from home. It would be fantastic. Licensing could be dealth with through some TBD mechanism.
There are tens of millions of machines in the world that are not being updated because of this problem. Companies with thousands of workstations just can't deal with the painful realities of having to reinstall applications.
This business of OS and hardware upgrades requiring full from-scratch application re-installations is, well, getting old.
Why do we have to reinstall applications such as Notepad++ or our JetBrains tools? Why do we have to reinstall any application at all?
Simple app migration as described above would see PC and OS sales would go through the roof.
Today we are contemplating migrating to W10 on new hardware. It will be a costly nightmare. And we will be stuck with this hardware for many years. If it weren't for this we would probably migrate hardware every 2 years rather than when absolutely forced to do so, as it is starting to be the case now with some of our software.
Think about it. The status quo makes no sense. Not in the context of the next generation in computing.
It used to be that way with DOS, each app was in a different directory and you could copy all of the files to a different machine, or just stick a floppy disk in the floppy drive and run it.
Upgrading from Vista is hard because Microsoft doesn't support Vista going to 10. You'd have to get a Windows 7 upgrade DVD and then update it to the point it gives you an option to upgrade to Windows 10.
I'd like to see more tools like Ninite: https://ninite.com/
It can install Notepad ++ but I don't think they added Jetbrain to it yet.
You find the same problem with GNU/Linux where each app installs library files and then text files for configuration.
Windows still suffers from DLL Hell where different DLL files conflict between installed apps. You have to place the DLL files in the same directory as the program to get around that.