Straight is best, but O-rings are pretty forgiving. NONE of my homemade EFI conversions have injectors consistently straight and square much to my dismay. But they don't leak! The O-rings should get a slight crush fit as they go into the bung to seal up.
Some folks use a 14mm drill bit, I use a 17/32 bit. I have clips on my injectors to guarantee that they won't go too far into the rail and stick the o-ring into the fuel passage, but I do try for the good practice of leaving a step at the end of the injector hole to let the o-ring stop against. Usually I'll drill a 3/8th hole all the way through, then follow it up with a 17/32" bit stopping short of going all the way through.
The rails are always drilled nicely on my drill press, I've struggled with the intake bungs lining up perfectly parallel, or exactly the same spacing as the rail. I tried using a jig I though was square, but still had issues. I'll try a different centering method next time. Again, none of them leak, so the O-rings are doing their job fantastically.