@tester74 - okay - much clearer.
Scenario 1 - that is correct. the only thing I would look into - as your didn't provide the additional detail is that if your income exceeds $200,000 (SINGLE), you will pay the 3.8% NIIT tax on the part of your unearned income that exceeds $200,000. Further since you indicate the 35% ordinary income tax bracket, how high is your income and does it push the capital gains into the 20% capital gains tax bracket?
and you are correct offsetting short term losses with long term gains in not tax efficient.
but best to sell based on your market view of the investment and let the tax consequences fall where they may. if you believe there are "losers" just sell them now and move on. if you don't consume all your losses, they are carried over in any event; they are not lost. what you are assuming is no change in the market value of your losses. If the price changes, then your assumptions about the tax consequences change. Taxes are the tail to the dog in my view.
