By single pass, I mean that the sockets are the width of the tool. Making them any wider makes it a multi pass. I was going to say that going to multi pass automatically doubles the time, but I just realized that it doesn't, until the socket is more than 2x the tool diameter.
As you alluded to, tearout is the bigger issue here. The visible side of the vertical piece is mounted against the horizontal piece, which should nearly eliminate all tearout.
You'll be able to do this if you cut them separately. A spacer will only be required when cutting them as a set.I would have thought that making the initial alignment simple and bulletproof and letting the CNC figure out the precision cuts would be an advantage. For me, that would mean using a straight reference to line up the top or bottom edges of the pieces exactly,
While using a CNC can greatly speed up the dovetail process, it's still time consuming, and for those cutting a lot of them, the faster it cuts, the better.