What I am saying is I sold it the first time and bought again after which price dropped significantly. I am still hodling from the second attempt, how do i claim this thousands of dollar loss to offset the few hundred gain?
You sell, then buy in again. If for example, you bought $100 worth in January and it had plummeted to $50 by December, you can sell it then claim a $50 capital loss. You then buy the same amount again. Don't trust random strangers on the internet though, you're better off talking to professionals.