In other words, if TSLA goes to $440 by 2016:
$50k shares limits me to $50k profit and holds up my original $50k for those 2 years.
$10k in leaps could limit (or extend) losses to the entire $10k I'm willing to lose and increase potential return several fold, right?
Sorry I missed this since I was reading on my phone earlier. Anyway, let's look at this a bit closer. (btw, thanks for the numbers since it makes it more concrete.)
In order for you to make several fold if TSLA goes to $440 by Jan16, then you'll probably need to buy Jan16 320 strike options for $20/each.
So, if TSLA is at $440 on Jan16 then each option is worth $120 ($440 stock price - 320 strike price). So that would be a 5x gain.
Let's make it more concrete.
With $10,000 capital, Jan16 320 strike option would cost $20 and each contract controls 100 shares so you could buy 5 contracts.
If/when TSLA is at $440 on Jan16, then you could sell those 5 contracts for $12,000 each ($120 x 100) for a total of $60,000. Your profit would be $50,000, which you would need to pay long-term capital gains (federal) and california state income tax. So if I assume your taxes are 25% then you'd pay $12,500 in taxes. So your total money in the end would be $47,500. (You could also choose to sell 4 and exercise 1 contract, but that's for another discussion)
Now, let's compare that to just holding common stock.
Let's say that you have $50,000 worth of TSLA stock, probably around 225 shares (at today's price). If/when the stock price is $440 in Jan16, then your stock will be worth 225 shares x $440 = $99,000. That would be a $49,000 gain. And then if you liquidated your stock you'd need to pay your taxes on the gains (depending on your cost basis). But technically, you're not forced to sell in Jan16 because they're stock, so you could just hold and defer taxes.
When you compare these two scenarios, then holding $10k in Jan16 320 strike LEAPs is the better choice since the $47,500 gain is post-tax vs the $49,000 gain pre-tax for your stock.
However, the situation changes drastically if/when TSLA is lower than $440 on Jan16.
Let's say TSLA is at $300 on Jan16. Then, your LEAPs would be basically worthless upon expiration on Jan16. You've lost your $10,000 completely.
But if you held your shares you'd have a nice profit of 225 shares x $75/share = $16,875. A 34% return. Not too shabby for 1.5 years of investment.
Let's take something a bit higher. Let's say TSLA is at $350 on Jan16.
Your LEAPs would be worth $30 ($350 stock price - $320 strike) x 5 contracts (or 500 option shares) = $15,000 gain. Minus 25% tax. $11,250 net.
Your common stock would be worth $350 x 225 shares = $78,750. Or $28,750 gain from your current $50,000 position. And you could defer your taxes by holding.
So in this case your far better off just keeping your stock in TSLA.
The situation is far more complicated than this, because if you sold your stock now and invested $10k in LEAPs, then you would have the remaining money to invest or do something with. So that could have value as well. Just how much value, that is something that could and should be calculated using various scenarios.
But anyway, from this example in order to make a 5x pre-tax gain with Jan16 LEAPs assuming TSLA is at $440 upon expiration, then you'd have to take quite a big risk with buying Jan16 320 strike options for $20. This means if TSLA ends lower than $340 on Jan16 expiration then you'd lose some of your initial $10k investment, and if ends at $320 or lower then you'd lose all of the $10k investment.
Now, risk/reward is in the eye of the beholder. If you like these odds (ie., you're confident of your price estimate or you don't mind losing $10k), then it could be a good deal/decision for you.
I think my point is that the ultimate decision is up to you according to your own set of risk/reward values and price projections, but the least you can and should do is to work out the numbers for various stock price scenarios to make sure you understand the risks/rewards clearly so you know what you're getting yourself into.