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"Empty always wins" you will be fine here...if the field is empty the value from you list upload will write to that field and ultimatly Salesforce based on you lead lifecycle management rules.
Yes, if you use Field Blocking on Salesforce Import/Sync, then the value will not be changed if the value exists.
I am trying to figure something like this for a couple of our fields. Where should i fix this - field blocking on Salesforce Import/sync?