JF
You mentioned transfers a number of time and it was touched upon very quickly by some others here; don't forget your payload. That includes luggage!
You wont get much into an R44. Think about where the pax are coming from and going to and what they will have with them, ie. laptops, suitcases, golf clubs, etc. Then do some practice weight and balances on the different scenarios and factor in your fuel. Show these to the boss and explain why some models don't work and why others do. That way you are not just focusing on price, but practicalities.
Are you flying over water? Will the owner/boss/pax want/need pop-out floats or just life jackets? Do you have or need an AOC?
Don't just think about the short term, once the boss sees the potentials, he may out grow that helicopter pretty quickly.
Personally I would go for a AS350B3 or EC130B4.
