@BLite
Going back a step, if you have the resources to pay off your house which would enable you to somehow change your life or take a less lucrative job that’s more enjoyable, do you actually need to pay off the house to be comfortable? For example, you could set up a system of automatic withdrawals and transfers, so that at the end of each month you sold just enough stock to cover the next mortgage payment, transferred it to a checking account, and had the mortgage payment automatically debited. That way your mortgage would be covered and you wouldn’t have to think about it, but you wouldn’t be taking such a large lump sum of capital gains and you would retain your mortgage interest deduction.
You can also talk to your stockbroker about selling your stocks on a LIFO method (last in first out) which will minimize the current capital gains.
