Investors & landlords

Question 1 - Not sure what the grantor trust letter means in connection with your covered call option.  We have seen Grantor Trust Tax letters regarding certain types of investments structured as Trusts, i.e., SPDR Gold Trust and the Grayscale Bitcoin Trust.   With regard to the SPDR and the GBTC, the trust letter explains how investors should report their pro rata share of sales of the underlying asset to pay trust expenses.  However, we are not familiar with the trust letter as it relates to your Fidelity account.

Question 2 - Yes, to report the covered call transaction, refer to your monthly account statement and also your trade confirmation.  Of the two trade documents, the trade confirmation is the more important one as it relates only to a single transaction and "confirms" the transaction with the customer.  However, maintain both documents.

Question 3 - Given the dates of your trades, your covered call is a short-term transaction.  Whether Fidelity reports the transaction as they should or not, you still need to report the transaction.  Their failure to report this transaction should not cause an error with your return.  Rather, your return will be all the more the accurate because you have reported this transaction.

Question 4 - Agreed, if you get an error in TurboTax which indicates something to the effect that your purchase date cannot be later in time than your sell date, then reverse the dates so that your purchase precedes the sale.  It should not matter that the dates are switched.  What matters is that the cost basis is reported correctly, the proceeds are reported correctly, and that the dates are accurate in that the dates reflect the "time period" of this transaction.

Question 5 - Yes, you can, and should, report this transaction even though you do not have an "official" tax reporting statement such as a 1099-B or similar document.  From your post, you seem to have everything you need to report the transaction.  Because it appears you do not have a document that can be uploaded into TurboTax, you will have to manually enter this transaction; however, because it is just one transaction, the process should not be time consuming.  Option trades are usually reported to the IRS--that is basis is reported--but you might want to confirm this fact with Fidelity.  

Yes, do keep your supporting documentation, that is, your monthly account statement, and trade confirmation.  Any other record from Fidelity that shows the transaction should also be maintained.  Assuming you are a resident alien, then yes, you can use TurboTax to prepare your tax return.  For non-resident aliens, TurboTax has partnered with Sprintax, and it is Sprintax that can prepare the tax return for a non-resident alien.  

@saulgoodman