I currently own a small single family rental house in the city from which we moved. It has become a hassle to travel back home every time a faucet drips, but not too far away to pay highway robbery to call in a plumber. We would like to sell that house, upgrade to a bank owned property with a substantial amount of built in equity for our main residence, and rent out our current residence. The question comes in where we would need to use the proceeds from the sale of the rental to make the down payment on the house that would be our new primary residence, but don't want to get clobbered with capital gains taxes in the process. Does anyone know how this could be juggled around to make this a possibility?