The supercharger will be installed by their master mechanic, not the idiot who forgets to fill up the oil after draining it. Ask the dealer if any superchargers have been installed there before. I had mine installed a dealership that hadn't done a Tundra before, but had done an FJ Cruiser. No problems (not to say I wasn't a bit worried, but it turned out okay).
The install is a pain because its fairly extensive...that being said there is nothing that is really all that difficult about it and is something that a guy can do by himself in a weekend with some standard tools and basic automotive experience. The entire kit is "bolt on" and doesnt require elements like measuring bearing clearances, machining or other factors where vast experience and knowledge of the motor is essential.
Again I would not recommend everyone to do the install but for someone that has the time it can be fun.
If any of the service people have any experience with yodas they shouldnt have any problems with the install.