1. Yes. Passive rental income and loss are carried to Form 8582, Passive Activity Loss Limitations to determine if you have an allowable loss.
On the Sch E, you can see all income is added, all losses subtracted and then allowed carryover is entered on lines 22 and 25.

2. As the owner, you are required to track the loss on each property in your records. So, yes, each property should have its own loss, but in your books, not on Sch E.
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