$220 strike price JAN15? What's the probability FB stock will be in the $ (higher than $220 by that time?) since you're betting it's current $190 stock price will be higher? In my experience the vast majority of options contracts expire worthless. The reality is no one would offer a option contract that would give the contract buyer an edge to profit, and hence most options expire with little or no profit; or more likely, you won't find any offering on the contract. Typically options pricing are better suited to stocks that have high volatility, but then typically, no one write contracts on such volatile stocks where the pricing is so in to the $.

FIF does not apply to derivative / options and hence why IRD/NZ Gov't has place regulation to deter or limit the investments in this area by NZ residents. The FMA states any foreign broker offering options contracts directly to NZ residents would be doing so illegally, without these brokers being licensed by the FMA (which none of them would bother). You could use a local NZ broker to play the options but i'm certain at a much higher cost and you would not be exempt from taxation on any of the profits made from derivatives. The whole idea of the FMA is that prior to this regulations, IRD had no form of taxation on those that made $ from options contracts conducted offshore. Since they were nothing more than contract terms and that the specific asset could not have a 'balance' account value at any specific day, this meant IRD could not directly tax it under FIF, nor could the overseas foreign brokers would comply to NZ regulations (or so IRD could keep tabs of NZ residents making $ from overseas accounts). Since the biggest player the USA is not part of the CRS (Common Reporting Standard where banks/brokers have to remit client information to the foreign tax authority by tax ID#), US brokers are simply ignoring NZ client or restricting their account by excluding derivative investments.

Shorting Uber shares directly is simplistic (providing your broker has a pool of shortable shares ; note not all brokers are the same and you'll find the NZ brokers most likely don't have access or an allotment of shares to allow for short position). In terms of FIF, an account balance is always determined during a short position so therefore, tax by FIF will still apply.

Here's an interesting thing to separate the individual investors vs the Kiwi Saver / NZ managed funds. Regardless of the managed fund's performance, FIF applies to the fund regardless on years they gained and on years they've lost value for their clients. While to the individual if they invested directly to the same foreign stock or ETF, on years where their portfolio goes negative, they can switch FIF to 'Comparative Value' method and no tax will be paid for that year. No financial seminar i've attended have provided me a direct answer why the NZ tax system has been so inequitable across the landscape of investments ; such as investing into real estate, Kiwi Saver, directly invested abroad, etc. There's no real level playing field whatsoever!!