Thank you Martin for your answers.

* Discount income tax is postponed to day of sale. Even though the income 
>> is earned in 2019, it is only taxable in 2020. How to account for this?
>>
>
> Do you mean that you want to recognize the discount in 2019 and the 
> capital gain in 2020?
> You would do it by recognizing the discount as income in 2019 (it'll be 
> taxed as income IINM) and hold the asset at FMV instead of discounted rate: 
>
> 2019-06-30 * "ESPP buy"
>  Assets:US:Hooli:EsppFund -850 USD
>  Assets:US:Etrade:Hooli:Espp 10 HOOL {100 USD}
>  Income:US:Hooli:Salary -150 USD ; Espp income
>

Yes, I want to recognize the discount as income (because it is taxed as 
income), and remaining gain as capital gain.
But, the income will be only taxed in the year when it is sold. If it is 
recognized as income here, then it will show in 2019 income sheet. How to 
handle this?
 

>
>  
>
>> * Qualifying and Disqualifying dispositions - Based on the holding 
>> period, the difference between grand-date FMV and vest-date FMV is taxed 
>> differently. How to account for / track this?
>>
>
> You can use a synthetic currency to hold your granted shares, such as 
> HOOL.UNVESTED at price 0 USD (you don't want unvested to show up on your 
> balance sheet) and when it vests you can deduct the corresponding granted 
> unvested units.
>
>>
>>
After the vest date, all the shares are vested and sellable. But the 
purchase price is lower of FMV of grant-date ($100) and vest-date ($120). 
So in this case, you were able to buy at $100 when the current market price 
is $120. This difference has to be tracked differently because this 
difference is taxed as qualifying or disqualifying dispositions based on 
the sale date.

Thanks in advance.

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