If you subscribe to Lr Classic you should have automatic access to Lr CC, provided your computer meets the minimum system requirements. You would not need to switch subscriptions unless you require Lr CC only, with 1TB of storage.
You then need to migrate your Lr Classic catalog to Lr CC. That will get all your originals into the cloud and switch off sync in Lr Classic. See link below for further information:
Just to expand on what Jon has said regarding urgrading to the 1TB option..... if you keep on your current plan, it will only give you 20GB of Cloud Storage.
Are you planning on dropping Classic altogether? As the 1TB Photography Plan (including Classic & Photoshop) cost double the 1TB Lightroom CC Plan.
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Something else you may want to consider. The new Lightroom CC isn't necessarily an "upgrade". It is an alternative program that you may want to consider. It is part of the Adobe Creative Cloud photography plan, and you can download and use it and consider it. Examine it carefully before you decide to switch to it or convert to it completely. It doesn't have all the features that Lightroom Classic CC has. Lightroom CC might have everything that you need and everything you are looking for. But my advice would be for you to use it and perhaps "experiment" with it for a while before you commit yourself to it fully.
I have been given very similar advice regarding the new lightroom CC multiple times. At this point I think I'm just going to stick with the regular lightroom program for now, thanks!