It sounds as if the transom plug has a check valve in it?? If so, get rid of it. I have never trusted these, with very good reason. If any water collects in the cockpit, most will be bailed out with the bilge pump--if there is not a manual switch, there needs to be one. The float switch will let the water be too high. Not too sure what the layout in the latest 22's with a hull liner is, but the older boats had a small sump just in front of the drain plug.
Definately take the sink drain apart and fix it yourself. You should be able to find a gasket at the hardware store, or make a gasket out of cork rubber or rubber gasket material. The use of silicone is not acceptable to "repair" an improper gasket seal.
The trim tab indicator--you paid for it, it should work--again an agrivation, but not essential. I have only had the sensors in one boat--I have owned a number of boats with tabs, and didn't have the tabs.
Be sure that both tanks work properly, Be sure that the stove and water pump work correctly. Take a hose and be sure that there are no leaks. Then fill the boat with fuel and your gear and take off. I would want to run the boat for a day or two before heading for Desloation sound--but there are plenty of places to hide if bad weather. I probably would trailer the boat as far as I could--cheaper to trailer than run on the water, and you can trailer even if the wind is blowing hard. The Georgia Straits can get pretty rough for a "sea trial" with a new boat.
Other wise, go take your vacation, take pictures and share them with us!
Most of us have gone thru a number of Quality control issues. Too bad that the Quality Control has not improved more. It is nothing new, but we have been assured that it was in "hand". Send a copy of your post to Rich Reynolds and ask him to review the thread, and who did the final inspection on your boat?
Enjoy the boat--I agree that all in all they are great boats.