You will get a better finish on the final cuts if you can manipulate the job so you are cutting on only one side of the cutter at a time. As most dovetails will have either a clearance slot in the sharp corner of the "female" dovetail or the corner knocked off the male counterpart for clearance, there is no need to try to cut right into that corner on both surfaces in one cut.
So for instance you would cut the 45 degree surface to size with the cutter lifted a few thou off the horizontal surface. Then drop the cutter a few thou to take the final cut along the horizontal surface with no contact between cutter and the 45 degree surface. Then you run a mini hacksaw or the likes down the point where the two surfaces meet so any step is removed and clearance is created. That way your dovetail is sure to ride on the two flat surfaces and not bear on the point in the V of the dovetail.
As to how many roughing cuts and finishing cuts, that all depends on many things such as size and rigidity of machine, nature of material, quality and type of cutter. In general it takes longer but is usually safer to take a number of roughing cuts then a number of finishing cuts so you can get the "feel" of things before you get to the critical stage. If your machine sails through it all like butter, you can up the ante. If it chatters and complains, you can slow things down.
It might pay to do a few test pieces first to try some different cut depths and feed rates to find what suits your machine and set up.
Edited By Hopper on 05/02/2019 10:51:59