When I am not sure of what is permitted or legal I have had good luck working with the town building inspector.
Take a hand drawn sketch of your lot and the proposed construction footprint to your town's building inspector and ask them the questions. It is free, and it will also get them on board with what you would like to do. It is a lot easier to have them working with you than it is to fight through a project. In Gilford, Dave Andrade the Building Inspector has been excellent. When I have worked with him he told me what couldn't be done and made suggestions about what would work and be legal.
As far as the taxes, it makes a difference whether you add on or start again. The tax assessment will be on what the final product is valued at. Obviously, if the whole structure has been replaced with brand new the market value will be higher.
It will be reassessed after the construction is complete. When the Building Department issues the Occupancy Permit they notify the assessing office that it should be revalued.
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