As the second part of the question - if booked via OTA, will I be covered by Trip Cancellation and Trip Interruption coverage?
I did send a message to customer service. Got following reply
The Visa(r) benefits on your account are managed by Visa(r). To ensure you receive the most accurate and up-to-date information regarding the coverage, contact Visa(r) directly by calling 844-357-2015 (collect at 701-461-1126).
Please contact us again if we can be of further assistance.
Honestly, quite a discouraging reply. Chase at least has benefit administrator desk and can and will answer on questions on this matter. US Bank just simply sends you to direction of Visa - go, deal with them.
BTW, question about OTAs got the similar type of reply as well:
You receive travel credits for transactions directly with airlines, hotels, car rental companies, taxis, limousines, passenger trains and cruise lines. Since U.S. Bank cannot control how merchants choose to classify their transactions, we cannot guarantee that a specific transaction will qualify.
And regarding OTAs - following
Transactions to Travel Agencies and Tour Operators do not qualify for the Travel Statement Credit.
At least they clearly say this.