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Q1 yes, to some degree. Kindle does not do ePUB.
Q1.1 Each reader has some quirks with regards to the specifications. Some have more than others. iBooks is known to ignore quite some specifications. Be advised, I am talking about v2 of the specification. Version 3 is just finalized, but there is only 1 physical reader that accepts this, at least some of it.
Q2 and Q2.1 This can be done with JavaScript in ePUB 3. As I said earlier, only 1 physical reader supports this at the moment. The extent of support is not yet clear.
Q3 This will be quite some work.
Q4 Best option will be an app.
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