I am wondering if this would be a viable, legal strategy. Say you bought 100 coins at $10 per coin over a year ago, then sold 50 coins at $1000 each. You're capital gains for this year would $49,500.
But then, at 11:55 PM on new years eve, you but 30 coins at $800 each ($24,000), and then just a few minutes later in 2014, you sell them again for the same amount of cash.
Nothing offset 20 of the 50 coins you first sold, so that would be $20,000 profit.
The other 30, I would think you'd have realized $200 of long term gain on each one. So another $6,000.
$26,000 in long term captial gains for 2013,
30 x $800 = $24,000 in long term capital gains to start off 2014.
I wonder if there will be little spikes and crashes as different time zones approach midnight.
No, this would not work.
Your capital gains for the year is $49,500.
You don't take a loss when you buy coins, regardless of the price you buy them at. You only take a loss when you SELL coins at a price less than what you paid for them.
I recommend you get an accountant.