Here's where this can be awful - I have a few pieces of software that are identical to this. After a few years I switch machines out and can't reactivate them and I'm SOL.

OP here - for boringBar you can use the same license for your new machine. It would not be an issue. Keep in mind though boringBar on your previously activated device will stop working after 30 days if it exceeds the device limit on your license.