Those of us whose experience dates back decades adhere to our own rules-of-thumb to avoid headaches we'd suffered in the past. I remember "upgrades" that gave me headaches and programs no longer compatible with the new OS.
This, of course, might be overtaken by new expectations with a new OS, but then -- you'd never know for sure, except from testimonials by others such as we see here.
Given that we put a lot of data on a shared server and workstation storage is ample in the house, I simply created new partitions or added new drives to install and activate Win 10 separately. If one anticipates the usual "day or two's time" to reinstall all software from scratch, one can take one's time this way, while still working with Win 7 and those existing software installations.
But it's good to hear that the "upgrade" path works smoothly for most folks, anyway.