i) What's your budget? If 7m or above, then go for the CL300. It will fulfil all the specifications given by yourself, and the DOCs are comparable to the Hawker.
ii) your 2-3 trips/weeks with the given stage lengths means that the airplane will fly around 300h/year, right. You'll want to have some sort of dispatch reliability then, right? As you are in the Caribbean, what brand's service center is within your reach? Chose accordingly!