I finally found some pictures of the room before I started working on it. Now I'm able to show off the 99% completion of the bedroom turned office. The process took a few months but the end result is almost exactly what I had in mind when starting. One of the important lessons I learned during the transition was to never apply painters tape to the ceiling in order to get a nice clean line near the intersection of the ceiling and wall. Not only did it not work, but in two places where I removed the blue painters tape, some of the paint peeled off as well. This was pretty depressing but the only thing I figured I could do was apply a few layers of paint to these areas. Although I know exactly where these areas are on the ceiling, they are not immediately noticeable to guests.
Another disappointment I had regarding the ceiling is how the painted surface turned out. Instead of one continuous surface, it looks like you can see where I rolled, especially at the edges of the roller. I think I used a bad technique with the roller brush extender or I used a bad roller cover not meant for ceilings. Either way, I'm, not thrilled with the end product of the ceiling but after two coats, I said the hell with it.