Just a thooought
I've read all this thread, and being new to this game just want to pose a question.
How come nobody is looking at the Legacy by Embraer?
The gov't just did a deal to use it over water for surveillance with Lockheed Martin systems aboard. They're setting up to build airframse in FL....but perhaps not the Legacy. The basic elements engines/avionics/APU/interior is US built anyway.
It has a $20mil price tag. That's millions less than anything being discussed.
It does the distance. having an effective range well over 3,000nm.
It has a virtually Gulftstream look alike cabin. Great (HUGE) baggage capacity and you can access during flight.
It has lowest operating costs (forget Conklin checkout the real figures with an actual operator). The regionals wouldn't use it (in ERJ format) if it was so expensive to operate they live and die in cents not $$$ on operating cost.
There are hundreds of the ERJ's all over the world, and with millions and millions of hours experience and no accidents.....certainly nobody has ever been hurt on an Embraer jet that I've heard about. The ERJ fleet guarantees a solid support structure, and the experience on the airframe is unbeatbale.
It has lots of systems redunacy (required for an airliner). I've flown on a few and the ride, comfort and cockpit are great.
I don't know about the Hawaii route...lot of water...but as far as IFSR for the engines they're Rolls Royce and currently performanig at least 4 times better than required for a 180 ETOPS !!! Hence if a twin engine stands a chance, then the Legacy should certainly be on the serious review list. At least that would seem logical.
Or is this a big ego thing.....
As I can see from your question you are very much trying to get best value for money that can do the job for the boss..... not just maximum number of not required features and toys for the boys.
A little noisy but a huge cabin and pretty long legs. And it hauls a TON of BBQ... Literally. 
