Thank you JamesG1 for your help. Just a few questions if you would be kind enough to answer. So if I have 50 separate transactions that I sold, do I need to list each one individually or can I lump them into one? And am I entering this data on Schedule D (Form 1040) as a "long term capital gain or losses" (since these items are 20+ years old that I have had them) or am I entering these either individually or lumped as one on form 1099-B?
Does Schedule D carry the numbers to 1099-B or vice versa?
Thank you @JamesG1
