Retro Windows application emulation seems to be very difficult to do. Either using BoxedWine on Windows, Wine itself on Windows, PCemu, virtual machines or x86box. Either the API surface is not enough implemented to handle all the quircks of old (sometimes 16-bit) software, or the x86 is not complete enough and unstable by itself, or the virtual machine software is too new so the old operating systems don't run properly.
I recently took the time to get a HP Compaq 530d and with some effort you get Windows 98 working on it just fine. And the applications also work fine. It has USB support, so I can just put it on my KVM. The only problem is VGA, a cheap Aliexpress VGA to HDMI converter doesn't support all resolutions - so if you get a BSOD or during POST, you need to connect a real monitor to find out what is going on.
I recently took the time to get a HP Compaq 530d and with some effort you get Windows 98 working on it just fine. And the applications also work fine. It has USB support, so I can just put it on my KVM. The only problem is VGA, a cheap Aliexpress VGA to HDMI converter doesn't support all resolutions - so if you get a BSOD or during POST, you need to connect a real monitor to find out what is going on.