In the last year:
dBpoweramp for, finally, ripping my whole CD collection to lossless. Advantages over itunes: much faster, better feedback on read errors.
VueScan for using my old scanner with modern Windows. Just worked.
OrCAD because Cadence was running a low-cost promotion.
I also upgraded my home use license for Mathematica.
I bought cyberduck last week as I had enough of FileZilla’s update nagging and main thread hogging shenanigans
Jetbrains Toolbox subscription
TurboTax
https://www.virtualhere.com/usb_server_software
Usb over Ethernet! I run it in my homelab and it's worth every penny. Amazing tool.