I live in MA that has a income tax as well as the US tax. My...

I live in MA that has a income tax as well as the US tax. My father taught me something that I have never forgot. Never delay a sell decision based on taxes. When it is time to sell do it. I have since read books that support this and if you do some math you will quickly see it is true.

Suppose you have a stock that is just short of long term gain that will lower your effective tax rate from 42 % to 21 %, state and fed combined. say your stock is 10,000 of which 15% is capital gain. So holding saves you 1,500 times ..5 or $750. now lets say the stock falls 10 % while you are waiting that cost you $1,000

Now I believe you said you live in DE all your CG is over a year old. You have told us you have been buying recently so most of your short term stock is Short term loss which will offset short term gain, then long term gain. So if you do not live in Delaware tell me where you live then give your buy dates. I will add numbers like saying sale was worth US 10,000 to prices. we will watch and decide if your holding was correct.

Just my experience but only novice investors worry about delaying sales to make sale long term gain or put it in a different tax year. Experience teaches this is not a good idea.

Last thing Investors that make good money know they have to file Quarterly taxes. This means delaying a gain only saves 45 days on average. Apparently you have never run into this. Kind of surprised that someone that owns apartments in NYC is not very use to Quarterly tax filling.