Transferring installed programs to another windows?

Question

Windows

There is an installed Win10x64 Ent. I want to try the Creators Update, if I like it I will use it. But! There are 150 programs installed on the current Windows, I don’t want to update it so that later I don’t waste time on a rollback (the Anniversary Update could not be rolled back at all, it took 3 days to demolish it and rearrange the necessary software). Option one: Install Windows on an adjacent partition>AU>CU. Will it be possible to transfer the software and settings without rearranging? Spending several days installing software to find out that something important has stopped working is unrealistic.
PS It is possible to change release of Windows (Ent> Pro) without rearrangement?

Answer 1

All attempts to transfer software with settings are attempts at random. Some things will carry over, some won't.
Something stores settings in files next to the software, something is stored in the user's directory, something is stored in the directory of all users, something is in the registry.
Between different versions of Windows, all this can change.
There is no reliable and guaranteed way that will work for all software.

Answer 2

Comrade Saboteur gave the correct answer to the question.
But the answer to the question "how to update and return back" will be "Backups" . Make a copy with the same Acronis and return to it if necessary.