The big concern here is that you are on the newest version of ConDoc. 4.0 should link pretty seamlessly with 4.5 and SU 2019 – no need to recreate any views. If your project drawings have changed since you initially created them in LayOut 2018 and ConDoc 4.0, you would just need to update your model in SU 2019, and re-export the desired scenes to LayOut and re-insert them. That would be the easiest way to do it. Unfortunately there is no automatic way to replace/resize/reposition views in LayOut, as they are linked directly to your SketchUp model.
The new Model Organization Guides will definitely help to make sure everything is where it needs to be. If your previous projects/drawings seemed to do what you needed them to do that that’s great proof that you know how the org system works! The MOG are a new tool to help aid in the process, as it can be difficult to someone who doesn’t know how our grouping/layering process works. Give it a try if you want, they’re great to use and helpful, but definitely optional.