1. Grammatically, both should be "whom". But, when the preposition, "to", is so far from the object, people don't notice that they are using the wrong form. Maybe it would be better grammatically to say, "To whom does this umbrella belong?" But no one really talks like that. Also, in English, we usually start with the question word. So, "This umbrella belongs to whom?" will probably only be used to make sure you heard correctly, or to express surprise or disbelief.
2. It depends on the context. Maybe he's always nice, but is being especially nice right now. Maybe he is not usually nice, but is right now. Most likely, he is either being nicer than usual or nicer than expected.