Every crime has elements. Because of this, if you meet the elements, you can be charged with multiple counts for your actions. For instance, one of the elements for a robbery charge is that you broke into a house with the intent to commit a crime. So, lets say, you broke into someones house to to fight them. In theory, you could be charged with an assualt and a robbery.
Additionally, you see this come up in sexual assualt cases all the time. A person can be charged as follows: Count One, touch a breast, Count Two, touched buttocks. etc.
Hope this helps.
Since 18.2-248 is drug distribution, if he has multiple cases under the same section than the allegation is that it happened more than one time. Specifically it is saying that it happened 3 times. You should look at the offense date on each charge to see if they are different.
This response is general in nature and is not legal advice. No attorney client relationship is formed by it.