Originally Posted by Milk Man (Post 3176058)

Long term stock CCL, Carnival Cruises? What you think? Got enough cash to last till 2022

Originally Posted by Milk Man (Post 3176058)

Long term stock CCL, Carnival Cruises? What you think? Got enough cash to last till 2022

Originally Posted by JamesBond (Post 3176020)

Yesterday I sold some puts that close this week, (in two days) and some that sell next Friday. I also have some longer term stuff (Feb 19). I do a lot of trading though. In 2020 I will wind up with somewhere near 1700 trades. I think I said in another post, but I TRY to make an average of $75/week for every $20,000 that I am leveraging, whether or not it is thru puts or calls. Some days you are the windshield, some days you are the bug. I am long and underwater in a position right now, but I will keep selling calls on it until it returns. If the pain goes on long enough, I will punt and move on. That's the art in all of this... Hope this helps.

Originally Posted by mispoken (Post 3176044)

As for writing covered calls, I NEVER write calls against shares I want to hold long term, eventually they may get called away and I don’t want to trade a few hundred bucks in premium for 10000% gains in the long run.

The nice thing about tastyworks, is that when you select a strike, they give you a POP and P50, that is probability of profit (making at least one penny) and probability of making 50% profit. This strike is usually called a “30 delta”, but don’t let that confuse you; what you want to do is pick a strike that shows up with a 70% POP. This is the tastytrade way, small trades often aiming for 70% POP.

Originally Posted by Gunfighter (Post 3176104)

-How much are you leveraging your $20,000?
-How do much time does it take reporting 1,700 trades on your tax return?

$75 per week comes out to $3,900 per year, which is a respectable 19.5%. A few days of being the windshield vs the bug can take that down to the mid teens very quickly. An 80% success rate at the often touted 2% monthly returns is 19.2%. You seem to be in the ballpark with the research I've done. I'm still uncertain about the time commitment, bookkeeping requirements and the tax liability of trading outside of a retirement account.




In the past, I've just rolled the covered calls out to the next expiration cycle. You could also buy back the shares after exercise, which creates a CG problem in a taxable account. An exercised ITM option isn't the end of the world. I recently sold FEB 725 CC on a portion of my TSLA position. I'm planning on rolling out to March in about a month.

Thanks for all the TW pointers. There are lots of similarities between thinkorswim and tastyworks. I just figured out that Tom Sosnoff is the connection between the two.

Originally Posted by Gunfighter (Post 3176104)

I'm still uncertain about the time commitment, bookkeeping requirements and the tax liability of trading outside.

Originally Posted by Milk Man (Post 3176058)

Long term stock CCL, Carnival Cruises? What you think? Got enough cash to last till 2022

Originally Posted by mispoken (Post 3176135)

It sucks. I pay my taxes quarterly, taxed as ordinary income. Paying Uncle Sam and the state 4x/yr sucks. As for the End of year tax, it’s fairly simple. All brokerages I’ve used send a summary of capital gains and that all you need to plug in. They do usually send a statement broken down of all 5000+ trades I’ve done, but ultimately the summary of P/L is all you need

Originally Posted by Seneca Pilot (Post 3176129)

Futures and options on futures and indices are 1256 contracts. There is no single trade reporting like there is with individual stocks. You just get a 1099. 60% long term capital gains rate, 40% regular income rate. Get your tax advice from an expert but that is the treatment for options and futures.

Originally Posted by Gunfighter (Post 3176169)

FIFY (he types in a polite, respectful manner, not often seen on the interwebs)

I could have been a little more specific in the original tax question. I'm still at the equity option level, I'm saving futures for when I really hate my kids and want to blow their inheritance. Options on equities are not 1256 contracts based on my pilot level understanding of the tax code. Options on ETFs and individual equities are taxed as ST CG. The difference in tax treatment is one reason it may make more sense to sell options on SPX vs SPY (index vs equity). I'll ask my CPA the next time we talk, probably Jan/Feb. It looks like single trade reporting summed up in an annual P/L is the requirement for my trades.