1. Yes so you do not want to do that. Short term is painful since you only get the cost basis where long term gets fair market value.
2. No. You need to make two entries. One for long term stock held more than a year and one for short term stocks - held less than a year.
To enter the long term:
Date acquired: you can choose various and long term or you can enter the date of the most recent purchase that is long term.
Cost basis: total all long term lots
Value: Total FMV on date of donation
To enter the short term:
Date acquired: Use the earliest date of the short term group
Cost basis: total of all short term lots
Value: total FMV on date of donation
The program will apply the limiting factors and limit the deduction to your basis.
For the Form 8283 - if value over $5,000 you will need to provide more specific details -# of shares and other useful information.
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