If I have a 1099-b for under $100. Do I really need to upgrade Turbo tax for $99 to file it?

In order to file the Sch D that you need, an upgrade is required.

TurboTax Desktop Deluxe can generate Schedule D as well as Form 8949.  You don’t need Premium to get basic Schedule D/Form 8949 support. 
https://turbotax.intuit.com/personal-taxes/cd-download/deluxe.jsp?bvstate=pg:4/ct:r#tax-forms

I think, but am not 100% sure, that Desktop Premium is required if you want TurboTax to automatically import your 1099-B.  With Desktop Deluxe I believe you need to type everything in manually.  

TurboTax Deluxe Online does not appear to support Schedule D:

https://turbotax.intuit.com/personal-taxes/online/deluxe.jsp#tax-forms