Technically, both questions should require the perpendicularity tolerance to be accounted for.
For question #1 the 30.6-30.0 hole - when the part is setup against the datum simulators - three areas of contact will be obtained from datum A, two against datum C and one area contact against datum D. These areas of contact are the outer-most areas of the as-built feature. Therefore the feature could tilt or taper the entire perpendicularity tolerance closer to the hole feature for datum features C and D.
So, imagine an imperfect part where datum features B and D are as-manufactured within the specified perpendicularity tolerance where the upper edge is at MMC and the lower edge is at LMC relative to the perspective hole features.