How do I install wood shutters on a brick house?
For those interested, here's the process I ended up using:


Measure, level and mark boards, appropriately aligning the future holes with the mortar between bricks.
Drill pilot holes into the wood shutters, including a 1/4" countersink to cover the screw heads up with wood filler. 

What I learned at this step: Unlike screwing wood to wood, where you can sink the screws into the wood easily without a countersink, when attaching wood to mortar, if you do not provide the countersink hole already and attempt to perform said action, you will strip the mortar and the screw will just spin and stay loose :( 

Next, re-level shutters and mark the mortar with the masonry drill bit through the pilot holes. I found that only drilling the top two holes worked best for me. I'll get to why in a minute. An extra set of hands comes in handy here :)
Set the shutter down and drill the top two mortar holes completely. 

What I learned at this step: Be sure to drill into the mortar enough to where the screw tip won't hit a dead-end (Most recommended a 1/16" or 1/4" of extra room beyond the screw tip). If you don't give a little extra space at the tip, you'll encounter a great deal of resistance, the screw will not go in all the way and you'll have to get the masonry bit out again.

Attach the shutter to the house using the top two holes. 
Now, we'll finish the bottom two holes: with your masonry bit, drill into the mortar through the board. 

What I learned at this step: I found this process to be the easiest for me, as my pilot holes didn't always match up completely when I attempted marking then drilling all four at the same time. Less margin of error on my part. But, this is became a personal preference. Decide for yourself.

Finish attaching the shutter to the mortar at the bottom with your screws.
Use wood filler to patch the holes, lightly sand filler. 
Paint/stain/seal accordingly. 

What I learned at this step: I had already applied a sealer to the back of the shutters before attaching them. I taped off my house using wide painter's tape after they were up and it saved me a huge headache of cleaning sealer off my house with mineral spirits.



Overall, I also learned:


I marked &amp; drilled all of the pilot holes into the shutters at one time which saved me on having to switch between the masonry &amp; wood drill bits. HINT: If you forget to take out the masonry bit and attempt to drill into wood, you very likely could start a friction fire! :D Haha!
Having two drills is a life-saver: I had my hammer drill set up with my masonry bit and my cordless drill had my Phillips bit in it ready for the screws.
Having a second pair of hands throughout the entire process was also a great deal of help.


Thanks for your help folks! I hope this little walk-through helps someone else, too!