I know it's been said but bears repeating. Can't go wrong going to a local tax professional. We should all consider this a conversation and not actual advice or what anyone should or should not do. Except for keep a log on paper. Or have an app or program that can be downloaded & printed /emailed. Each one of us has a different exact circumstance. So our tax liability or lack thereof, is gonna be different. I think I added to some confusion due to my paranoia. That's just a personality quirk of mine but my apologies. But if someone is not understanding your "advice" or thoughts. There is no need to be insulting. The whole subject of taxes, especially for someone facing 1099s for the first time can be very intimidating and we all need to be kind and patient. Or just skip their posts. Lyft and uber offer discounts on software and help filing.