Crypto taxes, no 1099K form, losses etc

You should be able to import the CSV file from Venmo into TurboTax Online Premium.  It sounds like you will have:

• Transactions with sales information for investment A but no cost information for investment A, and
• Transactions with cost information for investment B but no sales information for investment B.

Within TurboTax, you should be able to update these transactions through the Review and Edit processes within TurboTax.

Import the Venmo information on a CSV file as follows:

• Under Wages & Income, scroll down to Investments and Savings.  
• Click the down arrow and click Start/Revisit to the right of Stocks, Cryptocurrency, Mutual Funds, Other.
• At the screen Let's finish pulling in your investment income, click on Add investments.  
• At the screen Let's import your tax info, select Enter a different way.
• At the screen OK, let's start with one investment type, select Cryptocurrency.  Click Continue.
• At the screen Select your crypto experience, select Upload it from my computer.  Click Continue.
• At the screen What's the name of the crypto service you used, select Other at the down arrow.
• Enter 'Venmo' under name and select the correct CSV type.  Click Continue.
• Download the CSV information.

Click Review to view the downloaded data.

Click the pencil to the right to update missing cost and sales information.

Click the trashcan to the right to remove the transaction information.

Click Add another sale to add missing transactions that you discover when reviewing the CashApp bank account transactions.