This is a three part question.
1. I have been filing as a self-employed daily fantasy sports player since 2013. However, the past few years, my volume of play has fallen off steeply and I have ended up with a small loss each year ie less than $1,000 (I have not had 3 winning years out of the last 5, one of those years I lived in Vegas and could not play DFS). I have been continuing to file as self employed, reporting my net losses. I continue to keep track of my play on a daily basis with the intention of turning a profit. I have no other income source.
Can I (should I) continue to file as self-employed?
2. In 2021, I went to Vegas with full intention of playing poker for a month, keeping track of my wins/losses (3 years ago I had previously lived in Vegas and filed as a self-employed poker player). I then turned to video poker, studying how to be a winning player with full intention of turning a profit. I got a couple of wins that was past the threshold, and I had to fill out a form each time to make the IRS aware.
a. I had a net loss playing poker. Can I also include that on Schedule C? If so, do i have to separate my gains from losses or can I just net it out and put it under losses? The reason I ask is because with daily fantasy sports when I had a winning year, I received a 1099-MISC which was my NET for the year, which I reported under income on schedule C and the wins/losses were not separated. I'd like to do the same with poker/video poker to keep things consistent.
b. I had a net gain playing video poker (and the IRS is aware of the gains because of my wins over the threshold for reporting). Again, do I put my net amount won on Schedule C or do I separate the wins and losses on Schedule C. My concern is because my net is going to be less than what was reported to the IRS with the two wins I had to fill out paperwork for that it might get flagged.
3. I had also a few blackjack sessions and sports bets. Again with both of these endeavors, I studied and for sports betting did research, and kept track of my wins/losses. Should I also include that in my self employed income?
Whoever answers this, thank you so much for taking the time to read and answer my questions.
