When are you planning on going? I am not sure what airlines fly into the Portland Jetport.
Driving to SR from Portland takes about 75 minutes on a good day with a radar detector. Closer to an hour and a half if you are unfamiliar with the roads and there is some traffic. Sugarloaf is about 2-2.5 hours from Portland depending on some factors.
The driving time from Logan to SR (I live right next to the airport) is 3 hours and about 4 for Sugarloaf. It's really not that bad of a drive.
The snow up at SR and Sugarloaf has probably been the most consistent and reliable this year. If they get some more snow you will have a blast.
I like them both but I like The Loaf alittle more. If I were you I would hit both.
I drive 5-15 mph above the speed limit and Sunday River is 1 hour 40 minutes and Sugarloaf is 2 hours and 15 minutes from Portland. FWIW
Sugarloaf is worth the extra drive if you are spending more than 1 day.