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1031 into several cheaper properties and sell them off one by one in different years to lower taxes. Remote managers have been good enough for me.

Too much emotion attached now. 2:1 vote said sell. Probably time to sell and go from there.

I can understand that although I am sure you would not want to switch places.

My older brother chose work over college. I went to college and benefitted about $20k from my parents that he never saw. This has always been at the back of my mind. He is getting close to retirement and has always lived responsibly financially. But still things are a bit tight despite his low...

The biggest thing I miss is “take me to first unread message”

I think “They” are charging too much. 1000corks.com is a good place to search for bottle prices. Responding to Dash Man

I know it’s the blow that dough thread but that price is way too high. I see Florida online stores showing $70. https://www.craftspiritsxchange.com/the-balvenie-12-years-double-wood-750ml.html

The guy, walking, at the running track who manages to walk in in all eight lanes while I and others are running around as hard as we can.

Bunnahabhain 18 year old whisky was $180 a few years back. Last week at a total Wine $360!

Ah yes another option thanks

[/QUOTE are you mistaken that the long term tax is for a 100percent sale and short term is 50percect for two years. Wouldn’t the 400 sale be double Yes it is double. Part of the issue is that CA tax does not have LT. Only as income.

Thanks Hotwired Yes that is more or less what I worked through and decided on the split. Robo thanks for the tip. At this point I have bought and sold enough to generate half ($300k) cap gains and maybe with some flexibility if the accountant wants to structure it FIFO or LIFO. Now we wait...

Ultimately I am trying my best to pay taxes so they should be more or less happy :-)

No 1099 yet for crypto “ The IRS, via announcement 2023-2, deferred the requirement to report digital asset transactions on Form 1099-DA for the 2023 tax year. ” It does seem like it is some what flexible right now. “ Thankfully, the IRS accepts several methods for calculating the cost basis...

Good point I will check the FIFO status. I am not clear Re guards to crypto either. There is currently no wash sale rules for example.

Thanks all. We are happy with the overall balance of the portfolio. The sleep factor is doing ok. I have decided to sell and rebuy a portion of the crypto to generate $300k approx cap gains. That may also give some flexibility to the accountant choosing between first in first out or last in...

Fantastic results. And yes I miss the app also.

I am on here because my Tax advisor is on holiday :-) It does seem like The two year split and some simple stop losses maybe the best answer. Maybe the second half can hang on for LT status. Or mix it all. Sell a bit ST, Put a bit, Stop loss a bit. Thanks All.

My stumblings around the TD Ameritrade option order screen does not seem to provide an economical Put option. Just too expensive. Here is an example in case I am getting this completely wrong... SPY x 1200 shares ($473) = $568k value Put x 12 Contracts for Jan 2025, Strike $475 = $30,692 BITO...

More testing. According to this capital gains calculator (Inc California State Tax). https://smartasset.com/investing/capital-gains-tax-calculator#61dBqMySCV With no other income except capital gains. The tax bill (Married) is projected at: .............LT in 1y......vs....ST Split...

Ah yes I see that will kick in above $250k Married Filing Joint

Thanks. The gains have come since Oct. I am starting to understand the put limits and think it could work out well as a way to get to LT with downside protection. As some of this is crypto I could buy Puts on related ETFs like BITO or stocks like MSTR, MARA or COIN. I have a busy day ahead...

Leveraged stock ETFs eg UPRO and Crypto. So they would become LT if I wait.

Regarding the protective put idea I just read this. “ If the shares have been held for less than a year (say eleven months) and the trader purchases a protective put, even with more than a month of expiry left, the trader's holding period will immediately be negated. Any gains upon the sale of...

LT would be end of 2024. If we presume I will sell before LT then splitting the gains across two years seems justified. I had not thought of the Put idea. Thanks. I will have a think about that. But the idea is to get to LT with insurance against the gains disappearing. Seems wise.