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 just need to simply declare that in your latest trade you incurred a loss which would clearly offset the hundred dollars you have gained. By that you won't be incurring any capital gains tax if you incurred a net capital loss that's if you don't have any capital gain bearing assets in your asset portfolio, but if you have other assets such as stocks you can also offset it from these as you are calculating your total net capital for the tax period.