With respect to your first question, read through the following thread.
https://ttlc.intuit.com/community/investments-and-rental-properties/discussion/wash-sale-loss-disall...
With respect to your second question, that might depend upon the brokerage firm. Personally, on one instance in the past when I transferred some shares in-kind, the receiving brokerage firm reported the basis as N/A. Conversely, on another instance, the new brokerage firm managed to report the correct basis after the transfer.
