May I suggest taking a RAW file, follow the steps you ask about and see the result first hand?
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There are a few different workflows that work when using both Classic and CC. You should completely forget about the jpeg intermediate! You do not need that and it won't help.
Simplest workflow: Import into Classic. Put the raw files into a collection that you have set to sync with CC. Classic will generate smart previews that it will upload into CC. They will show up and be fully editable in Lightroom CC on the Desktop, Web, and mobile devices. Edits will sync back and forth with some caveats that not all metadata will sync but image edits all sync. The only disadvantage is that the images are just smart previews. For almost all purposes that is just fine.
Second workflow : Import always into CC. The raw files will sync up to the cloud and be downloaded automatically into Classic. Disadvantage of this is that the upload and download can take a very long time depending on your internet connection.
Third workflow is a hybrid. Start by importing into Classic and set a collection of images to Sync to CC. Then later when you have some time to wait for the upload, you can import the raw files into CC. It (should) will automatically realize that it already has the images and replace the cloud smart preview with the full raw file. Classic should keep syncing its changes and you should have a full raw everywhere.