Can DeskOps send my tax package to my CPA automatically?

Only if you turn it on, and only to the CPA name and email you add there. Three schedules: at each quarterly close, before each due date, or once at year end. The send runs on the server, once per tax period, and every delivery is logged; it is listed on the Communications screen with everything else DeskOps sends for you. The address it goes to is the one you set — Des cannot add a recipient.