Can you file taxes twice in one year?

You can't. Everything has to go on one return.

NO. Absolutely not. You chose basic tax software. It does not have the forms you need. Get the forms you need and file ONE tax return.

No, you can only file once. You can only file ONE return, EVERYTHING goes on one.

Just to confirm. You are saying you had 3000+ sales of uncovered securities and/or wash sale situations?

The form 8949 was changed so that all covered calls that didn't require and adjustment could be summarized on one or two lines.

You can only file one original return. Anything else is an amendment.

No. Everything for the year must be filed together. If you have stock transactions to file, then you are not allowed to file anything without them. If TurboTax won't accept them, then you must not file anything through TurboTax, and you must file everything through the other service.

No. If you try to file two tax returns the second will be rejected.

Your tax is based on your TOTAL income. That means you need to include all of your types of income on a single tax return.

Either pay for the version of Turbotax that does include schedule D, or use a different service.

No, if you've already filed once, any more filings for that year will be rejected. To add something you'll have to file an amendment.

Turbo tax comes in a whole slew of editions. One of them handles stock transactions.

Of course, it's not free....