Strategy to Redesign WP Membership Site?

We are redesigning our membership site which is built on S2 Member and Gravity Forms.
From my limited experience of working w/WP for the last few years, I know that there are mixed dependencies in the DB.
We can clone the site and update the UI on a dev site, but in the meantime, we will get new members which will modify our subscribers, S2 Member and Gravity Forms data.
My thinking is that we will have to manually copy the new UI back to the live site.
Anybody know of a more robust way to do this?
Thanks.

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