[tevake]

The Boat sounds well equipped, those shake down trips will give you a chance to get up to speed with all the equipment.

I totally understand your concerns about docking, and share them. My 45' tri is a real challenge to dock, especially in any wind. Probably a part of why I so prefer anchoring out. That and the lack of slips that fit a boat that is 27' wide :-)
One drill that might help is to find a clear area of water, then set your lunch hook with a fender or float on it. Then practice approaching from all wind angles. First come to it with your bow, then try to bring it alongside as you come to a stop.
Other than prop wrapping the line this is a low stress way to gain some comfort and confidence with your close quarters maneuvering. The twin props give you a bonus in maneuvering at low speeds. When you are practicing at your buoy approaches you can make adjustments to the boats position using one engine ahead and the other in reverse. Just play with it and you will get the feel for this boat.
Let your wife give it a try also. That way she will be less likely to laugh too much at your efforts :-)

Have fun!
Richard