how should i enter 1099-B if i have multiple Date Acquired for each stock? can i consolidate into 1 entry, if so what date i use?

Yes, you can consolidate.  The key is to divide short term and long term transactions which may require two entries.

1. Long term: held more than one year (one year plus one day)
2. Short term: held one year or less

Keep in mind that wash sales must be tracked separately if applicable. Wash Sale Rule Defined:

• A wash sale occurs when an investor sells or trades a security at a loss, and within 30 days before or after, buys another one that is substantially similar.
• It also happens if the individual sells the security at a loss, and their spouse or a company they control buys a substantially similar security within 30 days.
• The wash-sale rule prevents taxpayers from deducting a capital loss on the sale against the capital gain.

Affect on Cost Basis:

• The loss that occurs on a wash sale is added to the cost basis of the shares purchased that created the wash sale.
• When all shares are sold and there is no repurchase, that increased cost basis will be used in full and used to determine gain or loss.

As long as you are tracking the wash sales and are not using them on the tax return when you are not allowed, then you can simply enter the same cost basis as the selling price. This will  reconcile your tax return with your Form 1099-B Proceeds which is what the IRS is comparing.

Entering your consolidated transactions:

Open your TurboTax Online return:

1. Select Tax Home on the left panel > Select any Income category or Pick up where you left off
2. Select Tax Tools > Tools > Select Topic Search > Type 1099b  > Select GO (should be landed on 1099b)
3. Select Add Investments if your 1099-B is not yet present in your list
4. Continue to follow the prompts to enter the information yourself

Open your return in TurboTax Desktop:

1. Select Personal Income > Scroll to Investment Income > Select Stocks Cryptocurrency, Mutual Funds, Bonds, Other
2. Start or Update > Continue to follow the prompts to enter your 1099-B

The sale of any investment is required to be included with your tax return, gain or loss.  Information from the link below may be helpful

• What is Form 1099-B: Proceeds from Broker Transactions?