How do I fill out the Schedule D for this year, in which I have sold a DRiP? Do I use a different line for each buy transaction, or do I somehow average?

Well, Carole, let's look behind door number 3 for the correct answer. You report one sale per line, showing the purchase date as "various" and the basis as the total paid for the shares sold. Since this is a DRiP, if you sold everything you probably have a mix of short and long-term holding periods, so you'll have one entry on line 1 and one on line 8, splitting the sale proceeds pro rata.

TMF ExRO
Phil Marti