Yes, I admit there are examples where surcharges due to labor restrictions are necessary, and I suppose given the iron grip that the T's unions have, here would have to do as well. I just can't see how it could cost that much more to run a few buses for a few hours that a doubling of the fare wouldn't cover the costs.
I admit, I don't pretend to have numbers and data to show that a significant enough number of people would use the T during the wee hours. Maybe Boston really is a city that goes to bed early. I just find it hard to believe that an area roughly defined as the 617 area code (with a few immediate 781 communities like Medford, Malden and Revere) has a population of 1.5 million and can't support 24-hour transit on its subway lines (though, obviously run with buses) and maybe a few core bus routes, like the #1 and the #57.
In a sign of hope, San Francisco recently introduced 24-hour service within the city boundaries of SF (roughly the same size as the city of Boston). So, realistically the MBTA could and should offer at the very least some sort of similar service (though ideally routes into Cambridge, Somerville, Chelsea and maybe even Everett), for both the people who shouldn't be on the road and those who might have odd work hours (for myself, I used have to be at work at the airport for 5am. If it weren't for a coworker who was able to collect me on the way in, I never would have kept that job).
And yes, the Night Owl buses were a disaster. You had a bus running every 30 minutes from that ended at the time the bars were letting out. So, essentially it meant that people wanting to use transit would have to cut their nights short (particularly in the case of those needing to make transfers since all the lines 'hubbed' from Government Center) or were SOL (as in the case of restaurant workers who don't leave generally til after 3 - another job I had where 24 hour transit would have been useful for me).