A. I am sorry to say but there is a good chance your pet has an ear infection which caused the ear hematoma in the first place. Therefore I recommend at least treating the ear infection with topical antibiotics +/- antifungala prescribed by your vet.
Your pet is itching because the blood-filled ear is causing pain and discomfort. The best course of action, which is still considered conservative treatment, is to have the ear drained by your vet and then they can prescribe steroids and potentially oral antibiotics. This is a lot less invasive than the mattress suture pattern technique that is done to fix these, and I have seen lots of patients ear hematomas resolved this way as well.
A. It is not a good idea to let it heal naturally as it will scar and be irregular. In addition, there is an underlying cause that lead to the head shaking and cause of a hematoma in the first place. Usually it is an ear infection. This is unlikely to resolve without medical intervention:
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