Anonymous
Not applicable

Investors & landlords

definitely file to establish the capital loss carryover.  you see there's no way for the IRS to know that he didn't make a lot of money that was not reported to them.   also some people trade cryptocurrency on exchanges that do not report to the IRS so maybe he doesn't have a capital loss carryover.     it's cheaper to file now for free then in 2020 - Not free.