Can short sale info for stocks and options be entered correctly with sale date entered first with related info and acquired dated entered second

The date acquired of a short sale is the date you closed the short sale. A short sale is closed when you go to the market and acquire securities to replace the borrowed ones. The date of sale/disposal is the same date if you closed at a profit.

@fanfare provides additional details below:

• For stocks, the disposal date is two business days later (settlement) if you closed at a loss.
  • Note: Date Acquired and Date Disposed of refer to Columns (b) and (c) on Form 8949 that you will report to the IRS. 
• Your trade date is the date you closed the trade and goes in (b).
  • Settlement date must be calculated taking into account weekends and market holidays. 

I have desktop deluxe,   I have no problem entering a short sale using the date opened as the sales date and the date closed as the date acquired.  

that's the way my broker reports them

what's more, I import the trades and I get no red flags in Turbotax except when the cost basis is left bland (option expired) 

The thing is, not all brokerages supply you a 1099-B according to IRS requirements,

TD Ameritrade, for one, reports a short sale as described, above.

Some brokers will  make date disposed equal to date acquired.

If your gain/loss totals are accurate, and TurboTax passes it, I expect you can file that way.

References:

IRS Instructions for Form 8949,

"Column (c)—Date Sold or Disposed Of
Enter in this column the date you sold or
disposed of the property.
"For a short sale, enter the date you delivered
the property to the broker or lender to
close the short sale."

That would be the settlement date after acquiring the property.