If you can get the organization to switch to Debian, you could do it all with free software and manage the whole thing with Ansible.
I mention this because if the org is running Windows software that old, then current generation FOSS software is going to be a breathe of fresh air, by comparison.
It might not work if someone with a C title has a specific magical Windows package they want.
But even then, I would manage one or two Windows PCs (for a couple of C suite execs) by hand, than a full organization full. And you would save the organization a boatload of money.