My son is 16 and has his first W-2 and first 1099-B. Did not make much so was wondering if we had to buy the premium package in order to enter the 1099-B?

If you are using TurboTax Online, then yes, you have to use Premium in order to enter the 1099-B. Or you could use any version of the desktop TurboTax software.

You need to use TurboTax Premium if you are using the on-line product.  If you purchase TurboTax Desktop, you can file up to five federal returns with up to three state returns.

Yes, you can download and install TurboTax Desktop on up to five computers.  Refer to the TurboTax Help articles Can I install TurboTax on more than one computer? and How many tax returns can I file with TurboTax?

If you're using TurboTax Online, you can prepare one federal return and up to five state returns from your Intuit Account.

Refer to the TurboTax article How do I get started with TurboTax Desktop?

Refer to the TurboTax Help article Tax Filing Requirements for Children to review the filing requirements for children.