I would reccommend removing the old paint first, down to the bare alum.
I painted my motor last year. I blasted all the old paint off first, painted it with a zinc chromate primer (adheres to alum very well) then sprayed the color coats after the primer had dried.
I do not remember what blaster material I used to remove the paint....it was NOT sand though. It was just course enough to remove corrosion and paint.
I did not have access to the blaster to remove the paint off the head of flywheel cover, so I scuffed them as well as possible with a 3m scuff pad. The paint has not held up as well on the head or flywheel cover. It chips off easier than on the part I removed all the old paint & used zinc chromate primer.
A couple of old pics from the process.........