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It should sync after your quit the game every time and it shouldn't have a conflict every time you start the game.
Yes. You would want to choose to keep the local data and then it will use that to overwrite the cloud save.
Also, here's their official support page which might have the info you need:
https://support.rockstargames.com/articles/225410988/GTAV-PC-Cloud-Saves
It's about the old Social Club version of cloud saving, RGL is a new interface but I imagine it works mostly the same.