My boat is a Freedom and has special requirements with the unstayed flexible mast. While many sailmakers far away said that they could make sails for me, I wanted someone who knows the boat. There is a good sailmaker about three hours from me who is familiar with the boat, but I felt that I wanted someone closer. I am fortunate enough to be in an area where there are many Freedoms and several sailmakers know the boat well.
In your case, it is a tougher decision as the sailmaker who knows the boat is the one who is far away. I am not sure whether your boat has special needs. I felt that if I had my old Catalina 27, I could choose any sailmaker. Another thought is how heavy is your sail. My mainsail is over 700 sq. ft. and weighs a ton. That makes it prohibitive to send out for service, rather than use someone local. I could have saved several thousand dollars going offshore, but in the end, I went for the local loft.