First world problems here...
Let me start by saying I'm a pretty passive, buy and hold investor.
My ESPP stock from a former employer has done really well (to the tune of 230% over purchase price 4 years ago). The problem is now almost 20% of my stock portfolio is locked in to one company (albeit a good and stable one). I'd like to diversify, but want to avoid the tax hit from selling a stock with so much capital gain.
My stand by strategy has always been to wait until I have some losers in other stock or index funds, then sell the losers and ESPP together. As a result of the surge this past year or so, I don't have any liquid losers.
The only loser I have is a rental house that was bought at the height of the real estate bubble in 2007. If current trends hold, it too will reach its purchase price in a year or so. For now that is my most viable strategy though - sell it this summer, see how much losses I have, and sell equivalent ESPP stock gains.
Is there another strategy I'm not aware of?
Will selling them after ER (at least 5 years away) be more advantageous? The long term capital gains taxes are going to be the same, but having little or no income means I could use the standard deduction to counter these gains, no?