wash sales should not be a problem any more because brokers must adjust and report them. you only run into a problem if you have a wash sale because you have multiple taxable accounts or an IRA (sell at a loss in a taxable account and repurchase during the wash sale period in an IRA creates a wash sale. the reverse is not true). no software and no broker I know of tracks possible wash sales when the loss occurs in one a/c and the repurchase that creates the wash sale occurs in a different account.
as to short sales. I will not defend how my broker reports them to the IRS but it uses the same date for dates acquired and sold. it uses the acquired or expiration date as the sale date which at least means I'm reporting in the correct year.
there may still be a problem if you import. Turbotax does not like either the proceeds box or cost box to be blank which can occur if the short sale is an option that expires so the cost is zero but nothing gets imported
the same is true for purchase of an option that expires worthless sales price is left blank.
there may be a way around this. From what I can tell Turbotax doesn't import types A and D with no wash sale transactions as a single total in the area that it has for such reporting on the 1099-B worksheet. Fortunately, almost all my trades are of these types with no wash sale so I do not import. calculate the totals for the pure A and D types and enter just the totals. the 10-20 other trades I enter manually. you can not do a partial import.
