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Originally Posted by Vegas69
Very interesting to say the least.
Let's say you bought additional shares this year in a stock you have held for over a year and a day. Does it revert back to a short term gain or only on the new shares?
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When you go to SELL there is always a check box "choice" for selling "tax advantaged lots" or similar statement ---- meaning --- the brokerage will sell the shares with the dates that are the most tax advantages for you... unless of course you're sell "all".
The shares (brokerages do this for you) all have purchase dates.... per "lot" or per transaction date. So of course you'd only want sell the shares in your account that are LONG TERM rather than short term. Adding to the holdings doesn't change the entire holding -- only the shares that were bought on a/that particular date. They're not "retroactive".
You asked earlier about the dividends and dividends get different treatment because of course - the tax man always wants his pound of flesh --- so they're not going to let you get away with buying a stock a day before "ex-dividend" then scooping up that dividend and selling the shares... and then only letting you get away with paying 15% tax on that dividend portion. They made a rule about it... so that if that's what you were doing -- you're going to get slammed with the income tax rate not the dividend rate.
Now --- I've said this before. Taxes should never be a part of an investors strategy. An investors strategy is to maximize his income or gains or return on investment... and the taxes just are what they are. If you make a million bucks this year and you owe Uncle Sam 390K of it... SO WHAT! You still kept the rest... so in my view it's a choice... and I'd prefer to pay as much tax as humanly possible - because that means I made a fortune! LOL
What NONE OF US WANT TO DO however is to inadvertently cost ourselves a tax if we don't have to. So checking a date on the shares you plan to sell --- if you're just "pruning" or perhaps just want to change your portfolio... then why sell them one month "early" and get hit with a short term gain - when waiting a month would have saved you some tax money. Of course explaining all of this is harder than it looks --- because if a guy has a loss and he thinks he's going to lose MORE -- then there'd be no sense in holding on to the shares and taking a larger loss - just because it didn't work out on the income tax form.... conversely.... if you could sell shares and scoop up 100K gain... and maybe not get that gain if you waited until the exact right date for taxes... well then that might prove to be dumb.
It's more just something that should be "considered" before just hitting the sell button.
NOW -- for investing 102 -- We haven't touched on MANY other details. We've mostly just touched on buying - reaping the dividend - plowing that back into more shares and compounding these returns.
There's things like WASH SALES.... oh boy -- here we go! The WASH SALE rule to a way for the tax man to keep you paying max taxes. The Wash Sale Rule says that you can't sell a stock at a "loss" and then turn right around and buy the shares back. You must wait 30 days to buy them back - or you're DISALLOWED the "loss". But there's ways around this rule as well. Let's say you owned Chevron (CVX) and you have a loss at the end of the year - so on December 10th you sell -- writing off the loss against gains you had taken. Now that tax year is 2014 which ends on December 31st.... A new TAX year starts January 1st - so on the 2nd you buy Chevron shares. OH NO YOU DON'T!!! Not so fast --- the tax man says that's complete BS... and you just wanted to take the loss against 2014... and he's right of course. So they disallow the loss as a WASH SALE -- and the loss you took gets added to the cost of the new shares you just bought... It gets complicated --- so just don't do it. WAIT at least 30 days -- and that means 31 days... before you repurchase the shares of the company you just sold at a loss.
The way to beat this is --- you sell Chevron and buy anything else that is SIMILAR - but not substantially identical - if you need "oil" in your portfolio -- so you take the loss on Chevron and buy Conoco or Exxon... but you can't sell Chevon common and buy their preferred convertibles... that would be considered substantially identical.
If you've figure out a trick --- they've figured out how to counter that.