i was only referring to your example of losing $1000.
if it was from selling half of your shares, for instance, the $1000 loss on that transaction would carry over to subsequent years. Then when you sell the rest of the them, the profit/loss would be added to the $1000 carried over.
it all catches up in the end. the only wiggle room is when you make other gains/losses on other transactions, and are entitled to a 50% discount on some of them. then you have to make more complex decisions, because you can easily lose your 50% discount if you have too many carried over losses (which you need to utilize before you can utilize your 50% discount).
to be honest it is such a headache that these days i try to just hold shares for as long as possible. much easier on the wallet.
regarding your other question, yes, brokerage fees reduce your capital gain.
