As others have said, get rid of Windows in favour of Linux.
I use, as do others, Mint which itself is based on Ubuntu. I use Firefox & Thunderbird for browsing & email, Libre Office for letters and simple spreadsheets. Initially I used an old version of Paint Shop Pro via Wine, but now I use The Gimp – a sort of Photoshop equivalent. And DOSemu to run an old DOS based database.
For CAD I use DesignCad Pro 2000 again via Wine. I do have Design Cad Pro 3D v 17.2 which more or less runs via Wine, and I understand that Design Cad Pro 3D v 24 will also run via Wine. But anyway, these programs could also be run via Virtual Box & XP if required.
Skype does work via Linux, but for some reason has trouble connecting when the other person answers, and incoming calls aren't that good either, but if a pre-arranged call can be made, it's absolutely fine.
Finally, with Mint, upgrades are done on the fly if you want, when you want.
Yes it will take a bit of time to get it up and running successfully, but once done it will simply work, and work, and work… The biggest danger is that you will forget what you have done to get it working, it's that reliable.
Go on, give it a try, you know you want to.
Peter G. Shaw