Markovnikov's Rule

The general addition mechanism looks pretty straightforward, but what if the π-bond is asymmetrical? How can we tell which side the –X will add to?

Markovnikov’s Rule predicts that the carbocation will ALWAYS form on the more stable carbon, or the carbon that can eventually become more stable.

Note: Some professors teach that the “H will go to the side with the most H’s”. While this is usually true, I believe this misses the greater concept behind Markovnikov’s Rule, so I stay away from this explanation. 

Example: Provide the mechanism for the following addition reaction.