The dates should be included. Regarding the details of 1099-B, yes, the details should all be entered according to the time frame held. Form 1099-B will divide the transactions into short-term (held one year or less) or long-term (held more than one year). If it is not imported or otherwise entered in summary form, the details must be mailed in included with a "cover page," Form 8453, within 3 days of the electronic filing.
Form 8453 will be included in your return if you selected the option to enter a summary of stock sales. It will need to be printed and mailed in with your detail.
Click the links for more details:
How do I import my 1099?
Where do I enter a 1099-B?
What is Form 1099-B: Proceeds from Broker Transactions?
For state details that are required to be submitted, it would depend on your particular state. To contact your state's Department of Revenue, click this resource for Sate Department of Revenue Resources.
For information about Cryptocurrency, see: How is cryptocurrency like Bitcoin taxed?
