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Grab the free starter pack, import your profile and progress, all your TSW 4 DLC will work in TSW 5. After that there is no reason to keep TSW 4 installed, because sooner or later there will be no more patches or fixes.
Just install TSW 5 without any DLC (to reduce waiting times), start, import the profile (customised controls are also imported then) and close. Then you can uninstall TSW 4 completely and install the addons for TSW 5 you want.
Your content is playable on all of them.
I have 43 DLC that is TSW5 compatible. The content is separate from the base game.
If you uninstalled TSW4, and installed TSW5, the content is already purchased to your account and just installs as per normal.
All you have to do is go to the TSW5 store page and look at all the DLC and you will see your content with a blue bar indicating already purchased and compatible.