If a person has microangiopathic ischemic changes and involutional changes in his brain, could this cause frequent headaches?

Brain and headache: More likely it is your high blood pressure that is causing the ischemic damage to your brain and your headache. Have it checked in both arms. Or your BP meds. Send more details next time.

Small strokes: What you are describing are small strokes. These are usually asymptomatic but can cause more general symptoms over time but unlikely headaches.

No: At your age it would be more surprising if you DIDN'T have such changes. This is extremely common, and doesn't cause headaches. Someone your age who has the new onset of frequent headaches should see their doctor. There are a couple of diagnoses that should be ruled out.