Your rig looks awesome as well. I know the feeling about rushing a job to splash. I kinda rushed some things on my MA to get her painted before the winter. I researched your project before I did mine...I think you used AwlCraft 2000 ? If so you can wetsand and buff the finish to your desire. But from the pictures your paint work looks excellent...I also like the color
As you know immitation is the sincerest form of flattery.
The paint is actually Imron, but mixed to be as close to Awlgrip Ice Blue as possible.
Today, I did the deck with Moondust Awlgrip and grip tex. I gotta put another coat on, then pull the tape.
Doing the transom from the outside is perfectly OK, but you might also want to look into raising the transom 5 inches...thats what I did as per recommendation of others on this site.
If you don't want to remove the entire cap, you can try and cut the cap a few imches behind the wells (looking towards the bow), and just pop off the part of the cap which will give you access to the transom.
AVK